Substituted 3-phenylisoxazolines

ABSTRACT

Substituted 3-phenylisoxazolines I, and their salts and enol ethers, are described as herbicides ##STR1## where X═--O--, --S--, --N(R 9 )--; 
     R 1  ═CN, C 1  -C 4  -alkyl, C 1  -C 4  -haloalkyl, C 1  -C 4  -haloalkoxy, C 1  -C 4  -alkylsulfonyl; 
     R 2  ═H or unsubstituted or substituted C 1  -C 6  -alkyl, (C 1  -C 6  -alkyl)carbonyl, C 1  -C 6  -alkylsulfonyl, C 2  -C 6  -alkenyl, (C 2  -C 6  -alkenyl)carbonyl, C 2  -C 6  -alkynyl, (C 2  -C 6  -alkynyl)carbonyl; 
     R 3  ═H, halogen; 
     R 4  ═CN, halogen, C 1  -C 3  -haloalkyl; 
     R 5  ═H, CN, halogen, C 1  -C 3  -haloalkyl; 
     R 6  ═H, CN, halogen, C 1  -C 3  -haloalkyl or unsubstituted or substituted C 1  -C 6  -alkoxy; 
     R 7  ═CN, halogen; 
     R 8  in position α, R 7  in this case being in position β, or in position β, R 7  in this case being in position α, is 
     1) H, OH, SH, CN, NO 2 , halogen, C 1  -C 6  -alkyl, C 1  -C 6  -haloalkyl, C 1  -C 6  -haloalkoxy, C 1  -C 6  -haloalkylthio, C 1  -C 6  -alkylthio-(C 1  -C 6  -alkyl)carbonyl, (C 1  -C 6  -alkyl)iminooxycarbonyl, C 1  -C 6  -alkoxy-C 1  -C 6  -alkyl, C 1  -C 6  -alkoxyamino-C 1  -C 6  -alkyl, C 1  -C 6  -alkoxy-C 1  -C 6  -alkylamino-C 1  -C 6  -alkyl, 
     2) unsubstituted or substituted C 1  -C 6  -alkoxy, C 1  -C 6  -alkylthio, C 3  -C 6  -cycloalkoxy, C 3  -C 6  -cycloalkylthio, C 2  -C 6  -alkenyloxy, C 2  -C 6  -alkenylthio, C 2  -C 6  -alkynyloxy, C 2  -C 6  -alkynylthio, (C 1  -C 6  -alkyl)carbonyloxy, (C 1  -C 6  -alkyl)carbonylthio, (C 1  -C 6  -alkoxy)carboxyloxy, (C 2  -C 6  -alkenyl)carbonyloxy, (C 2  -C 6  -alkenyl)carbonylthio, (C 2  -C 6  -alkynyl)carbonyloxy, (C 2  -C 6  -alkynyl)carbonylthio, C 1  -C 6  -alkylsulfonyloxy or C 1  -C 6  -alkylsulfonyl, 
     3) 29 further radicals; 
     R 9  ═H, C 1  -C 6  -alkyl, C 3  -C 6  -cycloalkyl, C 3  -C 6  -alkenyl, C 3  -C 6  -alkynyl, C 1  -C 6  -alkoxy-C 1  -C 6  -alkyl, (C 1  -C 6  -alkoxy)carbonyl-C 1  -C 6  -alkyl, (C 3  -C 6  -alkenyloxy)carbonyl-C 1  -C 6  -alkyl, unsubstituted or substituted phenyl or phenyl-C 1  -C 6  -alkyl.

This application is a 371 of PCT/EP98/04489 filed Jul. 20, 1998.

The present invention relates to substituted 3-phenylisoxazolines of theformula I ##STR2## where: X is oxygen, sulfur or --N(R⁹)--;

R¹ is cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy or C₁-C₄ -alkylsulfonyl;

R² is hydrogen, C₁ -C₆ -alkyl, (C₁ -C₆ -alkyl)carbonyl, C₁ -C₆-alkylsulfonyl, C₂ -C₆ -alkenyl, (C₂ -C₆ -alkenyl)carbonyl, C₂ -C₆-alkynyl or (C₂ -C₆ -alkynyl)carbonyl, where the 7 last-mentionedradicals may, if desired, carry 1 to 3 radicals, in each case selectedfrom the group consisting of halogen, C₁ -C₆ -alkoxy, C₁ -C₆-alkylamino, di(C₁ -C₆ -alkyl)amino, C₁ -C₆ -alkoxyimino, phenyl,CO--OR¹⁰ or CO--N(R¹¹)--R¹² ;

R³ is hydrogen or halogen;

R⁴ is cyano, halogen or C₁ -C₃ -haloalkyl;

R⁵ is hydrogen, cyano, halogen or C₁ -C₃ -haloalkyl;

R⁶ is hydrogen, cyano, halogen, C₁ -C₃ -haloalkyl or C₁ -C₆ -alkoxywhich may, if desired, carry one or two substituents, in each caseselected from the group consisting of C₁ -C₆ -alkoxyimino, CO--OR¹³ andCO--N(R¹⁴)--R¹⁵ ;

R⁷ in position α or β is cyano or halogen;

R⁸ in position α, R⁷ in this case being in position β, or in position β,R⁷ in this case being in position α, is

1) hydrogen, hydroxyl, mercapto, cyano, nitro, halogen, C₁ -C₆ -alkyl,C₁ -C₆ -haloalkyl, C₁ -C₆ -haloalkoxy, C₁ -C₆ -haloalkylthio, C₁ -C₆-alkylthio-(C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆ -alkyl)iminooxycarbonyl, C₁-C₆ -alkoxy-C₁ -C₆ -alkyl, C₁ -C₆ -alkoxyamino-C₁ -C₆ -alkyl, C₁ -C₆-alkoxy-C₁ -C₆ -alkylamino-C₁ -C₆ -alkyl,

2) C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, C₃ -C₆ -cycloalkoxy, C₃ -C₆-cycloalkylthio, C₂ -C₆ -alkenyloxy, C₂ -C₆ -alkenylthio, C₂ -C₆-alkynyloxy, C₂ -C₆ -alkynylthio, (C₁ -C₆ -alkyl)carbonyloxy, (C₁ -C₆-alkyl)carbonylthio, (C₁ -C₆ -alkoxy)carboxyloxy, (C₂ -C₆-alkenyl)carbonyloxy, (C₂ -C₆ -alkenyl)carbonylthio, (C₂ -C₆-alkynyl)carbonyloxy, (C₂ -C₆ -alkynyl)carbonylthio, C₁ -C₆-alkylsulfonyloxy or C₁ -C₆ -alkylsulfonyl, where each of the 17last-mentioned radicals may, if desired, carry one to threesubstituents,

3) --CO--R²², --CS--R²², --C(NR²³)--R²², --C(R²²)(Z¹ R²⁴)(Z² R²⁵) whereZ¹ and Z² are each oxygen or sulfur, --C(R²²)═C(R²⁶)--CN,--C(R²²)═C(R²⁶)--CO--R²⁷, --CH(R²²)--CH(R²⁶)--CO--R²⁷,--C(R²²)═C(R²⁶)--CH₂ --CO--R²⁷, --C(R²²)═C(R²⁶)--C(R²⁸)═C(R²⁹)--CO--R²⁷,--C(R²²)═C(R²⁶)--CH₂ --CH(R³⁰)--CO--R²⁷, --CO--OR³¹, --CO--SR³¹,--CO--N(R³¹)--OR¹⁸, --C.tbd.C--CO--NH--OR¹⁸,--C.tbd.C--CO--N(R³¹)--OR¹⁸, --C.tbd.C--CS--NH--OR¹⁸,--C.tbd.C--CS--N(R³¹)--OR¹⁸, --C(R²²)═C(R²⁶)--CO--NH--OR¹⁸,--C(R²²)═C(R²⁶)--CO--N(R³¹)--OR¹⁸, --C(R²²)═C(R²⁶)--CS--NH--OR¹⁸,--C(R²²)═C(R²⁶)--CS--N(R³¹)--OR¹⁸, --C(R²²)═C(R²⁶)--C(R²¹)═N--OR¹⁸,--C(R²¹)═N--OR¹⁸, --C.tbd.C--C(R²¹)═N--OR¹⁸, --C(Z¹ R²⁴)(Z² R²⁵)--OR³¹,--C(Z¹ R²⁴)(Z² R²⁵)--SR³¹, --C(Z¹ R²⁴)(Z² R²⁵)--N(R³²)R³³, --N(R³²)R³³or --CON(R³²)R³³ ;

R⁹, R¹⁰, R¹², R¹³ and R¹⁵ independently of one another are eachhydrogen, C₁ -C₆ -alkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆-alkynyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆-alkyl, (C₃ -C₆ -alkenyloxy)carbonyl-C₁ -C₆ -alkyl, phenyl or phenyl-C₁-C₆ -alkyl, where the phenyl group and the phenyl ring of thephenylalkyl group may be unsubstituted or may carry one to threeradicals, in each case selected from the group consisting of halogen,nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy and (C₁-C₆ -alkyl)carbonyl;

R¹¹ and R¹⁴ independently of one another are each hydrogen, hydroxyl, C₁-C₆ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -alkoxy, (C₁ -C₆-alkoxy)carbonyl-C₁ -C₆ -alkoxy, C₃ -C₆ -alkenyl or C₃ -C₆ -alkenyloxy;

R²² is hydrogen, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₂ -C₆-alkenyl, C₂ -C₆ -alkynyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -alkoxy-C₁ -C₆-alkyl or (C₁ -C₆ -alkoxy)carbonyl;

R²³ is hydrogen, hydroxyl, C₁ -C₆ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆-alkynyl, C₃ -C₇ -cycloalkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy-C₁ -C₆-alkyl, C₁ -C₆ -alkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆ -alkynyloxy, C₃ -C₆-cycloalkoxy, C₅ -C₇ -cycloalkenyloxy, C₁ -C₆ -haloalkoxy, C₃ -C₆-haloalkenyloxy, hydroxy-C₁ -C₆ -alkoxy, cyano-C₁ -C₆ -alkoxy, C₃ -C₆-cycloalkyl-C₁ -C₆ -alkoxy, C₁ -C₆ -alkoxy-C₁ -C₆ -alkoxy, C₁ -C₆-alkoxy-C₃ -C₆ -alkenyloxy, (C₁ -C₆ -alkyl)carbonyloxy, (C₁ -C₆-haloalkyl)carbonyloxy, (C₁ -C₆ -alkyl)carbamoyloxy, (C₁ -C₆-haloalkyl)carbamoyloxy, (C₁ -C₆ -alkyl)carbonyl-C₁ -C₆ -alkyl, (C₁ -C₆-alkyl)carbonyl-C₁ -C₆ -alkoxy, C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkyl,(C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio-C₁ -C₆-alkoxy, di(C₁ -C₆ -alkyl) amino-C₁ -C₆ -alkoxy, phenyl which may itselfcarry one to three substituents, phenyl-C₁ -C₆ -alkoxy, phenyl-C₃ -C₆-alkenyloxy or phenyl-C₃ -C₆ -alkynyloxy, where in each case one or twomethylene groups of the hydrocarbon chains may be replaced by --O--,--S-- or --N(C₁ -C₆ -alkyl)-, and where each phenyl ring may beunsubstituted or may carry one to three substituents, heterocyclyl,heterocyclyl-C₁ -C₆ -alkoxy, heterocyclyl-C₃ -C₆ -alkenyloxy orheterocyclyl-C₃ -C₆ -alkynyloxy, where in each case one or two methylenegroups of the hydrocarbon chains may be replaced by --O--, --S-- or--N(C₁ -C₆ -alkyl)-, and where each heterocycle is unsubstituted oritself carries one to three substituents, or amino which may, ifdesired, be substituted, or an azaheterocycle;

R²⁴ and R²⁵ independently of one another are each C₁ -C₆ -alkyl, C₁ -C₆-haloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₁ -C₆ -alkoxy-C₁ -C₆-alkyl or

R²⁴ and R²⁵ together form a saturated or unsaturated 2- to 4-memberedhydrocarbon chain which may carry an oxo substituent, where one memberof this chain may be replaced by an oxygen, sulfur or nitrogen atomwhich is not adjacent to the variables Z¹ and Z², and where thehydrocarbon chain may carry one to three radicals, and where thehydrocarbon chain may also be substituted by a fused-on or spiro-linked3- to 7-membered ring which may contain as ring members one or twohetero atoms selected from the group consisting of oxygen, sulfur,nitrogen and C₁ -C₆ -alkyl-substituted nitrogen, and which may, ifdesired, itself carry one or two substituents;

R²⁶ is hydrogen, cyano, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁-C₆ -alkoxy, (C₁ -C₆ -alkyl)carbonyl or (C₁ -C₆ -alkoxy)carbonyl;

R²⁷ is hydrogen, O--R³⁴, S--R³⁴, C₁ -C₆ -alkyl which may carry one ortwo C₁ -C₆ -alkoxy substituents, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, C₁-C₆ -haloalkyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -alkylthio-C₁ -C₆ -alkyl, C₁-C₆ -alkyliminooxy, --N(R³²)R³³ or phenyl which may be unsubstituted ormay carry one to three substituents, in each case selected from thegroup consisting of cyano, nitro, halogen, C₁ -C₆ -alkyl, C₂ -C₆-alkenyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy and (C₁ -C₆-alkoxy)carbonyl;

R²⁸ is hydrogen, cyano, halogen, C₁ -C₆ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆-alkynyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, (C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆-alkoxy)carbonyl, --N(R³²)R³³, or phenyl which may itself carry one tothree substituents, in each case selected from the group consisting ofcyano, nitro, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₆-alkenyl, C₁ -C₆ -alkoxy and (C₁ -C₆ -alkoxy)carbonyl;

R²⁹ is hydrogen, cyano, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆-haloalkyl, (C₁ -C₆ -alkyl)carbonyl or (C₁ -C₆ -alkoxy)carbonyl;

R³⁰ is hydrogen, cyano, C₁ -C₆ -alkyl or (C₁ -C₆ -alkoxy)carbonyl;

R³¹ and R³⁴ independently of one another are each hydrogen, C₁ -C₆-alkyl, C₁ -C₆ -haloalkyl, C₂ -C₆ -alkenyl or C₂ -C₆ -alkynyl, where the4 last-mentioned groups may in each case carry one or two radicals, or(C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆ -haloalkyl)carbonyl, (C₁ -C₆-alkoxy)carbonyl, C₁ -C₆ -alkylaminocarbonyl, di(C₁ -C₆-alkyl)aminocarbonyl, C₁ -C₆ -alkyloximino-C₁ -C₆ -alkyl, C₃ -C₆-cycloalkyl, phenyl or phenyl-C₁ -C₆ -alkyl, where the phenyl rings maybe unsubstituted or may carry one to three substituents;

R³² and R³³ independently of one another are each hydrogen, C₁ -C₆-alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₃ -C₆ -cycloalkyl, C₁ -C₆-haloalkyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, (C₁ -C₆ -alkyl)carbonyl, (C₁-C₆ -alkoxy)carbonyl, (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkyl, (C₁ -C₆-alkoxy)carbonyl-C₂ -C₆ -alkenyl, where the alkenyl chain mayadditionally carry one to three halogen and/or cyano radicals, or C₁ -C₆-alkylsulfonyl, (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkylsulfonyl, phenylor phenylsulfonyl, where the two phenyl rings may be unsubstituted ormay themselves carry one to three substituents, in each case selectedfrom the group consisting of cyano, nitro, halogen, C₁ -C₆ -alkyl, C₁-C₆ -haloalkyl, C₃ -C₆ -alkenyl, C₁ -C₆ -alkoxy and (C₁ -C₆-alkoxy)carbonyl,

or R³² and R³³ together with the linking nitrogen atom form a saturatedor unsaturated 4- to 7-membered azaheterocycle which, in addition tocarbon ring members, may, if desired, contain one of the followingmembers: --O--, --S--, --N═, --NH-- or --N(C₁ -C₆ -alkyl)--;

and the agriculturally useful salts and enol ethers of the compounds I.

Furthermore, the invention relates to

the use of the compounds I as herbicides,

herbicidal compositions which comprise the compounds I as activeingredients,

processes for preparing herbicidal compositions using the compounds I,and

methods for controlling unwanted vegetation using the compounds I.

3-Phenylisoxazolines whose general formula formally also includes someof the present compounds I are already described as pharmaceuticallyactive compounds in WO 95/24398.

Furthermore, JP-A 07/041459 inter alia relates to certain3-phenylisoxazolines which differ from the present compound I inparticular in position 4 and which are also said to have pharmaceuticalactivity.

It is an object of the present invention to provide novel herbicidallyactive compounds which allow better selective control of unwanted plantsthan previous compounds.

We have found that these objects are achieved by the substituted3-phenylisoxazolines of the formula I defined at the outset.Furthermore, we have found herbicidal compositions which comprise thecompounds I and which have very good herbicidal activity. Moreover, wehave found processes for preparing these compositions and methods forcontrolling unwanted vegetation using the compounds I.

Depending on the substitution pattern, the compounds of the formula Ican contain one or more chiral centers, in which case they can exist inthe form of enantiomer and diastereomer mixtures. In the case ofcompounds I having at least one olefinic radical, E-/Z-isomers are, ifappropriate, also possible. This invention provides both the pureenantiomers or diastereomers and mixtures thereof.

Agriculturally useful salts are in particular the salts of those cationsand the acid addition salts of those acids whose cations and anions,respectively, do not adversely affect the herbicidal activity of thecompounds I. Suitable cations are in particular the ions of the alkalimetals, preferably sodium and potassium, of the alkaline earth metals,preferably calcium, magnesium and barium, and of the transition metals,preferably manganese, copper, zinc and iron, and the ammonium ion which,if desired, may carry one to four C₁ -C₄ -alkyl substituents and/or onephenyl or benzyl substituent, preferably diisopropylammonium,tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, andfurthermore phosphonium ions, sulfonium ions, preferably tri(C₁ -C₄-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C₁ -C₄-alkyl)sulfoxonium.

Anions of acid addition salts which may be used are primarily chloride,bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate,hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate,hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C₁-C₄ -alkanoic acids, preferably formate, acetate, propionate andbutyrate.

The organic moieties mentioned in the definition of R¹, R², R⁴ to R⁶, R⁸to R¹⁵ and R¹⁸ to R³⁴ and on phenyl, cycloalkyl and heterocyclyl ringsare collective terms for individual listings of the individual groupmembers. All hydrocarbon chains, ie. all alkyl, haloalkyl, hydroxyalkyl,cyanoalkyl, phenylalkyl, alkylideneaminooxy, alkenyl, haloalkenyl,phenylalkenyl, heterocyclylalkenyl or alkynyl moieties can bestraight-chain or branched.

Halogenated substituents preferably carry one to five identical ordifferent halogen atoms.

The term halogen represents in each case fluorine, bromine, chlorine oriodine, in particular fluorine or chlorine.

Examples of other meanings are:

C₁ -C₄ -alkyl: CH₃, C₂ H₅, n-propyl, CH(CH₃)₂, n-butyl, CH(CH₃)--C₂ H₅,2-methylpropyl or C(CH₃)₃, in particular CH₃, C₂ H₅ or CH(CH₃)₂ ;

C₁ -C₄ -haloalkyl: a C₁ -C₄ -alkyl radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, ie. for example CH₂ F, CHF₂, CF₃, CH₂ Cl, dichloromethyl,trichloromethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl,2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, C₂ F₅, 2-fluoropropyl,3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl,3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl,3,3,3-trifluoropropyl, 3,3,3-trichloropropyl,2,2,3,3,3-pentafluoropropyl, heptafluoropropyl,1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl,1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutylor nonafluorobutyl, in particular CH₂ F, CHF₂, CF₃, CH₂ Cl,2-fluoroethyl, 2-chloroethyl or 2,2,2-trifluoroethyl;

C₁ -C₆ -alkyl: C₁ -C₄ -alkyl as mentioned above and, for example,n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl,2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl,1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl,4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl, in particular CH₃, C₂H₅, n-propyl, CH(CH₃)₂, n-butyl, C(CH₃)₃, n-pentyl or n-hexyl;

C₁ -C₆ -haloalkyl: C₁ -C₆ -alkyl as mentioned above which is partiallyor fully substituted by fluorine, chlorine, bromine and/or iodine, ie.for example one of the radicals mentioned under C₁ -C₄ -haloalkyl or5-fluoro-1-pentyl, 5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl,5,5,5-trichloro-1-pentyl, undecafluoropentyl, 6-fluoro-1-hexyl,6-chloro-1-hexyl, 6-bromo-1-hexyl, 6-iodo-1-hexyl,6,6,6-trichloro-1-hexyl or dodecafluorohexyl, in particularchloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,2-fluoroethyl, 2-chloroethyl or 2,2,2-trifluoroethyl;

hydroxy-C₁ -C₆ -alkyl: for example hydroxymethyl, 2-hydroxyeth-1-yl,2-hydroxyprop-1-yl, 3-hydroxyprop-1-yl, 1-hydroxyprop-2-yl,2-hydroxybut-1-yl, 3-hydroxybut-1-yl, 4-hydroxybut-1-yl,1-hydroxybut-2-yl, 1-hydroxybut-3-yl, 2-hydroxybut-3-yl,1-hydroxy-2-methylprop-3-yl, 2-hydroxy-2-methylprop-3-yl or2-hydroxymethylprop-2-yl, in particular 2-hydroxyethyl;

cyano-C₁ -C₆ -alkyl: for example cyanomethyl, 1-cyanoeth-1-yl,2-cyanoeth-1-yl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3-cyanoprop-1-yl,1-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-1-yl,3-cyanobut-1-yl, 4-cyanobut-1-yl, 1-cyanobut-2-yl, 2-cyanobut-2-yl,1-cyanobut-3-yl, 2-cyanobut-3-yl, 1-cyano-2-methylprop-3-yl,2-cyano-2-methylprop-3-yl, 3-cyano-2-methylprop-3-yl or2-cyanomethylprop-2-yl, in particular cyanomethyl or 2-cyanoethyl;

phenyl-C₁ -C₆ -alkyl: for example benzyl, 1-phenylethyl, 2-phenylethyl,1-phenylprop-1-yl, 2-phenylprop-1-yl, 3-phenylprop-1-yl,1-phenylbut-1-yl, 2-phenylbut-1-yl, 3-phenylbut-1-yl, 4-phenylbut-1-yl,1-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl,1-(phenylmethyl)eth-1-yl 1-(phenylmethyl)-1-(methyl)eth-1-yl or1-(phenylmethyl)prop-1-yl, in particular benzyl or 2-phenylethyl;

phenyl-(C₁ -C₆ -alkyl)carbonyloxy: for example benzylcarbonyloxy,1-phenylethylcarbonyloxy, 2-phenylethylcarbonyloxy,1-phenylprop-1-ylcarbonyloxy, 2-phenylprop-1-ylcarbonyloxy,3-phenylprop-1-ylcarbonyloxy, 1-phenylbut-1-ylcarbonyloxy,2-phenylbut-1-ylcarbonyloxy, 3-phenylbut-1-ylcarbonyloxy,4-phenylbut-1-ylcarbonyloxy, 1-phenylbut-2-ylcarbonyloxy,2-phenylbut-2-ylcarbonyloxy, 3-phenylbut-2-ylcarbonyloxy,4-phenylbut-2-ylcarbonyloxy, 1-(phenylmethyl)eth-1-ylcarbonyloxy,1-(phenylmethyl)-1-(methyl)eth-1-ylcarbonyloxy or1-(phenylmethyl)prop-1-ylcarbonyloxy, in particular benzylcarbonyloxy or2-phenylethylcarbonyloxy;

phenyl-C₁ -C₆ -alkylsulfonyloxy: for example benzylsulfonyloxy,1-phenylethylsulfonyloxy, 2-phenylethylsulfonyloxy,1-phenylprop-1-ylsulfonyloxy, 2-phenylprop-1-ylsulfonyloxy,3-phenylprop-1-ylsulfonyloxy, 1-phenylbut-1-ylsulfonyloxy,2-phenylbut-1-ylsulfonyloxy, 3-phenylbut-1-ylsulfonyloxy,4-phenylbut-1-ylsulfonyloxy, 1-phenylbut-2-ylsulfonyloxy,2-phenylbut-2-ylsulfonyloxy, 3-phenylbut-2-ylsulfonyloxy,4-phenylbut-2-ylsulfonyloxy, 1-(phenylmethyl)eth-1-ylsulfonyloxy,1-(phenylmethyl)-1-(methyl)eth-1-ylsulfonyloxy or1-(phenylmethyl)prop-1-ylsulfonyloxy, in particular benzylsulfonyloxy or2-phenylethylsulfonyloxy;

(C₁ -C₆ -alkyl)carbonyl: CO--CH₃, CO--C₂ H₅, n-propylcarbonyl,1-methylethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl,2-methylpropylcarbonyl, 1,1-dimethylethylcarbonyl, n-pentylcarbonyl,1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl,1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl,2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, n-hexylcarbonyl,1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl,4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl,1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl,2,2-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl,3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl,1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl,1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl, inparticular CO--CH₃, CO--C₂ H₅ or CO--CH(CH₃)₂ ;

(C₁ -C₆ -alkyl)carbonyl-C₁ -C₆ -alkyl: C₁ -C₆ -alkyl which issubstituted by (C₁ -C₆ -alkyl)carbonyl as mentioned above, ie. forexample methylcarbonylmethyl;

(C₁ -C₆ -haloalkyl)carbonyl: a (C₁ -C₆ -alkyl)carbonyl radical asmentioned above which is partially or fully substituted by fluorine,chlorine, bromine and/or iodine, ie. for example chloroacetyl,dichloroacetyl, trichloroacetyl, fluoroacetyl, difluoroacetyl,trifluoroacetyl, chlorofluoroacetyl, dichlorofluoroacetyl,chlorodifluoroacetyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl,2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2,2-difluoroethylcarbonyl,2,2,2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl,2-chloro-2,2-difluoroethylcarbonyl, 2,2-dichloro-2-fluoroethylcarbonyl,2,2,2-trichloroethylcarbonyl, pentafluoroethylcarbonyl,2-fluoropropylcarbonyl, 3-fluoropropylcarbonyl,2,2-difluoropropylcarbonyl, 2,3-difluoropropylcarbonyl,2-chloropropylcarbonyl, 3-chloropropylcarbonyl,2,3-dichloropropylcarbonyl, 2,3-bromopropylcarbonyl,3-bromopropylcarbonyl, 3,3,3-trifluoropropylcarbonyl,3,3,3-trichloropropylcarbonyl, 2,2,3,3,3-pentafluoropropylcarbonyl,heptafluoropropylcarbonyl, 1-(fluoromethyl)-2-fluoroethylcarbonyl,1-(chloromethyl)-2-chloroethylcarbonyl,1-(bromomethyl)-2-bromoethylcarbonyl, 4-fluorobutylcarbonyl,4-chlorobutylcarbonyl, 4-bromobutylcarbonyl, nonafluorobutylcarbonyl,(5-fluoro-1-pentyl)carbonyl, (5-chloro-1-pentyl)carbonyl,(5-bromo-1-pentyl)carbonyl, (5-iodo-1-pentyl)carbonyl,(5,5,5-trichloro-1-pentyl)carbonyl, undecafluoropentylcarbonyl,(6-fluoro-1-hexyl)carbonyl, (6-chloro-1-hexyl)carbonyl,(6-bromo-1-hexyl)carbonyl, (6-iodo-1-hexyl)carbonyl,(6,6,6-trichloro-1-hexyl)carbonyl or dodecafluorohexylcarbonyl, inparticular trifluoroacetyl;

(C₁ -C₆ -alkyl)carbonyloxy: acetyloxy, ethylcarbonyloxy,n-propylcarbonyloxy, 1-methylethylcarbonyloxy, n-butylcarbonyloxy,1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy,1,1-dimethylethylcarbonyloxy, n-pentylcarbonyloxy,1-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy,3-methylbutylcarbonyloxy, 1,1-dimethylpropylcarbonyloxy,1,2-dimethylpropylcarbonyloxy, 2,2-dimethylpropylcarbonyloxy,1-ethylpropylcarbonyloxy, n-hexylcarbonyloxy, 1-methylpentylcarbonyloxy,2-methylpentylcarbonyloxy, 3-methylpentylcarbonyloxy,4-methylpentylcarbonyloxy, 1,1-dimethylbutylcarbonyloxy,1,2-dimethylbutylcarbonyloxy, 1,3-dimethylbutylcarbonyloxy,2,2-dimethylbutylcarbonyloxy, 2,3-dimethylbutylcarbonyloxy,3,3-dimethylbutylcarbonyloxy, 1-ethylbutylcarbonyloxy,2-ethylbutylcarbonyloxy, 1,1,2-trimethylpropylcarbonyloxy,1,2,2-trimethylpropylcarbonyloxy, 1-ethyl-1-methylpropylcarbonyloxy or1-ethyl-2-methylpropylcarbonyloxy, in particular acetyloxy;

(C₁ -C₆ -haloalkyl)carbonyloxy: a (C₁ -C₆ -alkyl)carbonyloxy radical asmentioned above which is partially or fully substituted by fluorine,chlorine, bromine and/or iodine, ie. for example chloroacetyloxy,dichloroacetyloxy, trichloroacetyloxy, fluoroacetyloxy,difluoroacetyloxy, trifluoroacetyloxy, chlorofluoroacetyloxy,dichlorofluoroacetyloxy, chlorodifluoroacetyloxy,2-fluoroethylcarbonyloxy, 2-chloroethylcarbonyloxy,2-bromroethylcarbonyloxy, 2-iodoethylcarbonyloxy,2,2-difluoroethylcarbonyloxy, 2,2,2-trifluoroethylcarbonyloxy,2-chloro-2-fluoroethylcarbonyloxy,2-chloro-2,2-difluoroethylcarbonyloxy,2,2-dichloro-2-fluoroethylcarbonyloxy, 2,2,2-trichloroethylcarbonyloxy,pentafluoroethylcarbonyloxy, 2-fluoropropylcarbonyloxy,3-fluoropropylcarbonyloxy, 2,2-difluoropropylcarbonyloxy,2,3-difluoropropylcarbonyloxy, 2-chloropropylcarbonyloxy,3-chloropropylcarbonyloxy, 2,3-dichloropropylcarbonyloxy,2-bromopropylcarbonyloxy, 3-bromopropylcarbonyloxy,3,3,3-trifluoropropylcarbonyloxy, 3,3,3-trichloropropylcarbonyloxy,2,2,3,3,3-pentafluoropropylcarbonyloxy, heptafluoropropylcarbonyloxy,1-(fluoromethyl)-2-fluoroethylcarbonyloxy,1-(chloromethyl)-2-chloroethylcarbonyloxy,1-(bromomethyl)-2-bromoethylcarbonyloxy, 4-fluorobutylcarbonyloxy,4-chlorobutylcarbonyloxy, 4-bromobutyl or nonafluorobutyl, in particulartrifluoroacetoxy;

(C₁ -C₆ -alkyl)carbonyloxy-C₁ -C₆ -alkyl: C₁ -C₆ -alkyl which issubstituted by (C₁ -C₆ -alkyl)carbonyloxy as mentioned above, ie. forexample methylcarbonyloxymethyl, ethylcarbonyloxymethyl,1-(methylcarbonyloxy)ethyl, 2-(methylcarbonyloxy)ethyl,2-(ethylcarbonyloxy)ethyl, 3-(methylcarbonyloxy)propyl,4-(methoxycarbonyloxy)butyl, 5-(methoxycarbonyloxy)pentyl or6-(methoxycarbonyloxy)hexyl;

(C₁ -C₆ -alkyl)carbonylthio: acetylthio, ethylcarbonylthio,n-propylcarbonylthio, 1-methylethylcarbonylthio, n-butylcarbonylthio,1-methylpropylcarbonylthio, 2-methylpropylcarbonylthio,1,1-dimethylethylcarbonylthio, n-pentylcarbonylthio,1-methylbutylcarbonylthio, 2-methylbutylcarbonylthio,3-methylbutylcarbonylthio, 1,1-dimethylpropylcarbonylthio,1,2-dimethylpropylcarbonylthio, 2,2-dimethylpropylcarbonylthio,1-ethylpropylcarbonylthio, n-hexylcarbonylthio,1-methylpentylcarbonylthio, 2-methylpentylcarbonylthio,3-methylpentylcarbonylthio, 4-methylpentylcarbonylthio,1,1-dimethylbutylcarbonylthio, 1,2-dimethylbutylcarbonylthio,1,3-dimethylbutylcarbonylthio, 2,2-dimethylbutylcarbonylthio,2,3-dimethylbutylcarbonylthio, 3,3-dimethylbutylcarbonylthio,1-ethylbutylcarbonylthio, 2-ethylbutylcarbonylthio,1,1,2-trimethylpropylcarbonylthio, 1,2,2-trimethylpropylcarbonylthio,1-ethyl-1-methylpropylcarbonylthio or1-ethyl-2-methylpropylcarbonylthio, in particular acetylthio;

(C₁ -C₆ -haloalkyl)carbonylthio: a (C₁ -C₆ -alkyl)carbonylthio radicalas mentioned above which is partially or fully substituted by fluorine,chlorine, bromine and/or iodine, ie. for example chloroacetylthio,dichloroacetylthio, trichloroacetylthio, fluoroacetylthio,difluoroacetylthio, trifluoroacetylthio, chlorofluoroacetylthio,dichlorofluoroacetylthio, chlorodifluoroacetylthio,2-fluoroethylcarbonylthio, 2-chloroethylcarbonylthio,2-bromoethylcarbonylthio, 2-iodoethylcarbonylthio,2,2-difluoroethylcarbonylthio, 2,2,2-trifluoroethylcarbonylthio,2-chloro-2-fluoroethylcarbonylthio,2-chloro-2,2-difluoroethylcarbonylthio,2,2-dichloro-2-fluoroethylcarbonylthio,2,2,2-trichloroethylcarbonylthio, pentafluoroethylcarbonylthio,2-fluoropropylcarbonylthio, 3-fluoropropylcarbonylthio,2,2-difluoropropylcarbonylthio, 2,3-difluoropropylcarbonylthio,2-chloropropylcarbonylthio, 3-chloropropylcarbonylthio,2,3-dichloropropylcarbonylthio, 2-bromopropylcarbonylthio,3-bromopropylcarbonylthio, 3,3,3-trifluoropropylcarbonylthio,3,3,3-trichloropropylcarbonylthio,2,2,3,3,3-pentafluoropropylcarbonylthio, heptafluoropropylcarbonylthio,1-(fluoromethyl)-2-fluoroethylcarbonylthio,1-(chloromethyl)-2-chloroethylcarbonylthio,1-(bromomethyl)-2-bromoethylcarbonylthio, 4-fluorobutylcarbonylthio,4-chlorobutylcarbonylthio, 4-bromobutylthio or nonafluorobutylthio, inparticular trifluoroacetylthio;

C₁ -C₄ -alkoxy: OCH₃, OC₂ H₅, n-propoxy, OCH(CH₃)₂, n-butoxy,1-methylpropoxy, OCH₂ --CH(CH₃)₂ or OC(CH₃)₃, in particular OCH₃ or OC₂H₅ ;

C₁ -C₆ -alkoxy: C₁ -C₄ -alkoxy as mentioned above and, for example,n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy,1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy,1-ethylpropoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy,3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy,1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy,2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy,1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxyand 1-ethyl-2-methylpropoxy, in particular methoxy, ethoxy or1-methylethoxy;

C₁ -C₄ -haloalkoxy: a C₁ -C₄ -alkoxy radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, ie. for example chloromethoxy, dichloromethoxy,trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy,chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy,2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy,2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy,3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy,2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy,3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy,1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy,1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy,4-bromobutoxy or nonafluorobutoxy, in particular 2-chloroethoxy or2,2,2-trifluoroethoxy;

C₁ -C₆ -haloalkoxy: a C₁ -C₆ -alkoxy radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, ie. for example one of the radicals mentioned under C₁ -C₄-haloalkoxy or 5-fluoro-1-pentoxy, 5-chloro-1-pentoxy,5-bromo-1-pentoxy, 5-iodo-1-pentoxy, 5,5,5-trichloro-1-pentoxy,undecafluoropentoxy, 6-fluoro-1-hexoxy, 6-chloro-1-hexoxy,6-bromo-1-hexoxy, 6-iodo-1-hexoxy, 6,6,6-trichloro-1-hexoxy ordodecafluorohexoxy, in particular chloromethoxy, fluoromethoxy,difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy or2,2,2-trifluoroethoxy;

phenyl-C₁ -C₆ -alkoxy: for example benzyloxy, 1-phenylethoxy,2-phenylethoxy, 1-phenylprop-1-yloxy, 2-phenylprop-1-yloxy,3-phenylprop-1-yloxy, 1-phenylbut-1-yloxy, 2-phenylbut-1-yloxy,3-phenylbut-1-yloxy, 4-phenylbut-1-yloxy, 1-phenylbut-2-yloxy,2-phenylbut-2-yloxy, 3-phenylbut-2-yloxy, 4-phenylbut-2-yloxy,1-(phenylmethyl)eth-1-yloxy, 1-(phenylmethyl)-1-(methyl)eth-1-yloxy or1-(phenylmethyl)prop-1-yloxy, in particular benzyloxy or 2-phenylethoxy;

phenyl-C₁ -C₆ -alkylthio: for example benzylthio, 1-phenylethylthio,2-phenylethylthio, 1-phenylprop-1-ylthio, 2-phenylprop-1-ylthio,3-phenylprop-1-ylthio, 1-phenylbut-1-ylthio, 2-phenylbut-1-ylthio,3-phenylbut-1-ylthio, 4-phenylbut-1-ylthio, 1-phenylbut-2-ylthio,2-phenylbut-2-ylthio, 3-phenylbut-2-ylthio, 4-phenylbut-2-ylthio,1-(phenylmethyl)-eth-1-ylthio, 1-(phenylmethyl)-1-(methyl)eth-1-ylthioor 1-(phenylmethyl)prop-1-ylthio, in particular benzylthio or2-phenylethylthio;

(C₁ -C₄ -alkoxy)carbonyl: CO--OCH₃, CO--OC₂ H₅, n-propoxycarbonyl,CO--OCH(CH₃)₂, n-butoxycarbonyl, 1-methylpropoxycarbonyl, CO--OCH₂--CH(CH₃)₂ or CO--OC(CH₃)₃, in particular CO--OCH₃, CO--OC₂ H₅,CO--OCH(CH₃)₂ or CO--CH₂ --CH(CH₃)₂ ;

(C₁ -C₆ -alkoxy)carbonyl: (C₁ -C₄ -alkoxy)carbonyl as mentioned aboveand, for example, n-pentoxycarbonyl, 1-methylbutoxycarbonyl,2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl,2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl,1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl,1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl,3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl,1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl,1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl,2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl,1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl,1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl,1-ethyl-1-methylpropoxycarbonyl or 1-ethyl-2-methylpropoxycarbonyl, inparticular methoxycarbonyl, ethoxycarbonyl or 1-methylethoxycarbonyl;

(C₁ -C₆ -alkoxy)carbonyloxy: methoxycarbonyloxy, ethoxycarbonyloxy,n-propoxycarbonyloxy, 1-methylethoxycarbonyloxy, n-butoxycarbonyloxy,1-methylpropoxycarbonyloxy, 2-methylpropoxycarbonyloxy,1,1-dimethylethoxycarbonyloxy, n-pentoxycarbonyloxy,1-methylbutoxycarbonyloxy, 2-methylbutoxycarbonyloxy,3-methylbutoxycarbonyloxy, 2,2-dimethylpropoxycarbonyloxy,1-ethylpropoxycarbonyloxy, n-hexoxycarbonyloxy,1,1-dimethylpropoxycarbonyloxy, 1,2-dimethylpropoxycarbonyloxy,1-methylpentoxycarbonyloxy, 2-methylpentoxycarbonyloxy,3-methylpentoxycarbonyloxy, 4-methylpentoxycarbonyloxy,1,1-dimethylbutoxycarbonyloxy, 1,2-dimethylbutoxycarbonyloxy,1,3-dimethylbutoxycarbonyloxy, 2,2-dimethylbutoxycarbonyloxy,2,3-dimethylbutoxycarbonyloxy, 3,3-dimethylbutoxycarbonyloxy,1-ethylbutoxycarbonyloxy, 2-ethylbutoxycarbonyloxy,1,1,2-trimethylpropoxycarbonyloxy, 1,2,2-trimethylpropoxycarbonyloxy,1-ethyl-1-methylpropoxycarbonyloxy or1-ethyl-2-methylpropoxycarbonyloxy, in particular methoxycarbonyloxy,ethoxycarbonyloxy or 1-methylethoxycarbonyloxy;

(C₁ -C₆ -alkoxy)carbonylthio: methoxycarbonylthio, ethoxycarbonylthio,n-propoxycarbonylthio, 1-methylethoxycarbonylthio, n-butoxycarbonylthio,1-methylpropoxycarbonylthio, 2-methylpropoxycarbonylthio,1,1-dimethylethoxycarbonylthio, n-pentoxycarbonylthio,1-methylbutoxycarbonylthio, 2-methylbutoxycarbonylthio,3-methylbutoxycarbonylthio, 2,2-dimethylpropoxycarbonylthio,1-ethylpropoxycarbonylthio, n-hexoxycarbonylthio,1,1-dimethylpropoxycarbonylthio, 1,2-dimethylpropoxycarbonylthio,1-methylpentoxycarbonylthio, 2-methylpentoxycarbonylthio,3-methylpentoxycarbonylthio, 4-methylpentoxycarbonylthio,1,1-dimethylbutoxycarbonylthio, 1,2-dimethylbutoxycarbonylthio,1,3-dimethylbutoxycarbonylthio, 2,2-dimethylbutoxycarbonylthio,2,3-dimethylbutoxycarbonylthio, 3,3-dimethylbutoxycarbonylthio,1-ethylbutoxycarbonylthio, 2-ethylbutoxycarbonylthio,1,1,2-trimethylpropoxycarbonylthio, 1,2,2-trimethylpropoxycarbonylthio,1-ethyl-1-methylpropoxycarbonylthio or1-ethyl-2-methylpropoxycarbonylthio, in particular methoxycarbonylthio,ethoxycarbonylthio or 1-methylethoxycarbonylthio;

C₁ --C₆ -alkylthio: SCH₃, SC₂ H₅, SCH₂ -C₂ H₅, SCH(CH₃)₂, n-butylthio,1-methylpropylthio, 2-methylpropylthio, SC(CH₃)₃, n-pentylthio,1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio,2,2-dimethylpropylthio, 1-ethylpropylthio, n-hexylthio,1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio,2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio,1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio,2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio,1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio,1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and1-ethyl-2-methylpropylthio, in particular SCH₃ or SC₂ H₅ ;

C₁ -C₄ -haloalkylthio: C₁ -C₄ -alkylthio such as methylthio, ethylthio,n-propylthio, 1-methylethylthio, n-butylthio, 1-methylpropylthio,2-methylpropylthio and 1,1-dimethylethylthio, preferably methylthio orethylthio, which is partially or fully substituted by fluorine, chlorineand/or bromine, ie. for example SCHF₂, SCF₃, chlorodifluoromethylthio,bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio,2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio,2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio,2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio,2,2-dichloro-2-fluoroethylthio, SC₂ F₅, 2-fluoropropylthio,3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio,2-bromopropylthio, 3-bromopropylthio, 2,2-difluoropropylthio,2,3-difluoropropylthio, 2,3-dichloropropylthio,3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio,2,2,3,3,3-pentafluoropropylthio, heptafluoropropylthio,1-(fluoromethyl)-2-fluoroethylthio, 1-(chloromethyl)-2-chloroethylthio,1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio,4-bromobutylthio or nonafluorobutylthio, in particular SCHF₂ or SCF₃ ;

C₁ -C₆ -haloalkylthio: C₁ -C₆ -alkylthio as mentioned above which ispartially or fully substituted by fluorine, chlorine and/or bromine, ie.for example one of the radicals mentioned under C₁ -C₄ -haloalkylthio or5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio,5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio or6-chlorohexylthio, in particular SCH₂ F, SCHF₂, SCF₃, SCH₂ Cl,2-fluoroethylthio, 2-chloroethylthio or 2,2,2-trifluoroethylthio;

C₁ -C₆ -alkylsulfinyl: SO--CH₃, SO--C₂ H₅, n-propylsulfinyl,1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl,2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, n-pentylsulfinyl,1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl,1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl,2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, n-hexylsulfinyl,1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl,4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl,1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl,2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl,3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl,1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl,1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl, inparticular SO--CH₃ ;

C₁ -C₆ -alkylsulfonyl: SO₂ --CH₃, SO₂ --C₂ H₅, n-propylsulfonyl, SO₂--CH(CH₃)₂, n-butylsulfonyl, 1-methylpropylsulfonyl,2-methylpropylsulfonyl, SO₂ --C(CH₃)₃, n-pentylsulfonyl,1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl,1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, n-hexylsulfonyl,1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl,4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl,1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl,2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl,3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl,1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl,1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl, inparticular SO₂ --CH₃ ;

C₁ -C₆ -alkylsulfonyloxy: O--SO₂ --CH₃, O--SO₂ --C₂ H₅,n-propylsulfonyloxy, O--SO₂ --CH(CH₃)₂, n-butylsulfonyloxy,1-methylpropylsulfonyloxy, 2-methylpropylsulfonyloxy, O--SO₂ --C(CH₃)₃,n-pentylsulfonyloxy, 1-methylbutylsulfonyloxy, 2-methylbutylsulfonyloxy,3-methylbutylsulfonyloxy, 1,1-dimethylpropylsulfonyloxy,1,2-dimethylpropylsulfonyloxy, 2,2-dimethylpropylsulfonyloxy,1-ethylpropylsulfonyloxy, n-hexylsulfonyloxy, 1-methylpentylsulfonyloxy,2-methylpentylsulfonyloxy, 3-methylpentylsulfonyloxy,4-methylpentylsulfonyloxy 1,1-dimethylbutylsulfonyloxy,1,2-dimethylbutylsulfonyloxy, 1,3-dimethylbutylsulfonyloxy,2,2-dimethylbutylsulfonyloxy, 2,3-dimethylbutylsulfonyloxy,3,3-dimethylbutylsulfonyloxy, 1-ethylbutylsulfonyloxy,2-ethylbutylsulfonyloxy, 1,1,2-trimethylpropylsulfonyloxy,1,2,2-trimethylpropylsulfonyloxy, 1-ethyl-1-methylpropylsulfonyloxy or1-ethyl-2-methylpropylsulfonyloxy, in particular methylsulfonyloxy;

C₁ -C₆ -haloalkylsulfonyloxy: C₁ -C₆ -alkylsulfonyloxy as mentionedabove which is partially or fully substituted by fluorine, chlorine,bromine and/or iodine, ie. for example ClCH₂ --SO₂ --O--, CH(Cl)₂ --SO₂--O--, C(Cl)₃ --SO₂ --O--, FCH₂ --SO₂ --O--, CHF₂ --SO₂ --O--, CF₃ --SO₂--O--, chlorofluoromethyl-SO₂ --O--, dichlorofluoromethyl-SO₂ --O--,chlorodifluoromethyl-SO₂ --O--, 1-fluoroethyl-SO₂ --O--,2-fluoroethyl-SO₂ --O--, 2-chloroethyl-SO₂ --O--, 2-bromoethyl-SO₂--O--, 2-iodoethyl-SO₂ --O--, 2,2-difluoroethyl-SO₂ --O--,2,2,2-trifluoroethyl-SO₂ --O--, 2-chloro-2-fluoroethyl-SO₂ --O--,2-chloro-2,2-difluoroethyl-SO₂ --O--, 2,2-dichloro-2-fluoroethyl-SO₂--O--, 2,2,2-trichloroethyl-SO₂ --O--, C₂ F₅ --SO₂ --O--,2-fluoropropyl-SO₂ --O--, 3-fluoropropyl-SO₂ --O--,2,2-difluoropropyl-SO₂ --O--, 2,3-difluoropropyl-SO₂ --O--,2-chloropropyl-SO₂ --O--, 3-chloropropyl-SO₂ --O--,2,3-dichloropropyl-SO₂ --O--, 2-bromopropyl-SO₂ --O--, 3-bromopropyl-SO₂--O--, 3,3,3-trifluoropropyl-SO₂ --O--, 3,3,3-trichloropropyl-SO₂ --O--,2,2,3,3,3-pentafluoropropyl-SO₂ --O--, C₂ F₅ --CF₂ --SO₂ --O--,1-(fluoromethyl)-2-fluoroethyl-SO₂ --O--,1-(chloromethyl)-2-chloroethyl-SO₂ --O--,1-(bromomethyl)-2-bromoethyl-SO₂ --O--, 4-fluorobutyl-SO₂ --O--,4-chlorobutyl-SO₂ --O--, 4-bromobutyl-SO₂ --O--, C₂ F₅ --CF₂ --CF₂ --SO₂--O--, 5-fluoropentyl-SO₂ --O--, 5-chloropentyl-SO₂ --O--,5-bromopentyl-SO₂ --O--, 5-iodopentyl-SO₂ --O--,5,5,5-trichloropentyl-SO₂ --O--, C₂ F₅ --CF₂ --CF₂ --CF₂ --SO₂ --O--,6-fluorohexyl-SO₂ --O--, 6-chlorohexyl-SO₂ --O--, 6-bromohexyl-SO₂--O--, 6-iodohexyl-SO₂ --O--, 6,6,6-trichlorohexyl-SO₂ --O-- ordodecafluorohexyl-SO₂ --O--, in particular CF₃ --SO₂ --O--;

C₁ -C₆ -alkylamino: e.g. NH--CH₃, NH--C₂ H₅, NH--CH₂ --C₂ H₅,NH--CH(CH₃)₂, n-butylamino, 1-methylpropylamino, 2-methylpropylamino,NH--C(CH₃)₃, NH--(n--C₅ H₁₁) or NH--(n--C₆ H₁₃), in particular C₁ -C₄-alkylamino;

(C₁ -C₄ -alkyl)aminocarbonyl: CO--NH--CH₃, CO--NH--C₂ H₅, CO--NH--CH₂--C₂ H₅, CO--NH--CH(CH₃)₂, n-butylaminocarbonyl, CO--NH--CH(CH₃)--C₂ H₅,CO--NH--CH₂ --CH(CH₃)₂ or CO--NH--C(CH₃)₃, in particular CO--NH--CH₃ orCO--NH--C₂ H₅ ;

(C₁ -C₆ -alkyl)aminocarbonyl: (C₁ -C₄ -alkyl)aminocarbonyl as mentionedabove and, for example, n-pentylaminocarbonyl,1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl,3-methylbutylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl,1-ethylpropylaminocarbonyl, n-hexylaminocarbonyl,1,1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylaminocarbonyl,1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl,3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl,1,1-dimethylbutylaminocarbonyl, 1,2-dimethylbutylaminocarbonyl,1,3-dimethylbutylaminocarbonyl, 2,2-dimethylbutylaminocarbonyl,2,3-dimethylbutylaminocarbonyl, 3,3-dimethylbutylaminocarbonyl,1-ethylbutylaminocarbonyl, 2-ethylbutylaminocarbonyl,1,1,2-trimethylpropylaminocarbonyl, 1,2,2-trimethylpropylaminocarbonyl,1-ethyl-1-methylpropylaminocarbonyl or1-ethyl-2-methylpropylaminocarbonyl, in particular CO--NH--CH₃,CO--NH--C₂ H₅ or CO--NH--CH(CH₃)₂ ;

di(C₁ -C₆ -alkyl)aminocarbonyl: for example N,N-dimethylaminocarbonyl,N,N-diethylaminocarbonyl, N,N-dipropylaminocarbonyl,N,N-di(1-methylethyl)aminocarbonyl, N,N-dibutylaminocarbonyl,N,N-di(1-methylpropyl)aminocarbonyl,N,N-di(2-methylpropyl)aminocarbonyl,N,N-di(1,1-dimethylethyl)aminocarbonyl, N-ethyl-N-methylaminocarbonyl,N-methyl-N-propylaminocarbonyl, N-methyl-N-(1-methylethyl)aminocarbonyl,N-butyl-N-methylaminocarbonyl, N-methyl-N-(1-methylpropyl)aminocarbonyl,N-methyl-N-(2-methylpropyl)aminocarbonyl,N-(1,1-dimethylethyl)-N-methylaminocarbonyl,N-ethyl-N-propylaminocarbonyl, N-ethyl-N-(1-methylethyl)aminocarbonyl,N-butyl-N-ethylaminocarbonyl, N-ethyl-N-(1-methylpropyl)aminocarbonyl,N-ethyl-N-(2-methylpropyl)aminocarbonyl,N-ethyl-N-(1,1-dimethylethyl)aminocarbonyl,N-(1-methylethyl)-N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl,N-(1-methylpropyl)-N-propylaminocarbonyl,N-(2-methylpropyl)-N-propylaminocarbonyl,N-(1,1-dimethylethyl)-N-propylaminocarbonyl,N-butyl-N-(1-methylethyl)aminocarbonyl,N-(1-methylethyl)-N-(1-methylpropyl)aminocarbonyl,N-(1-methylethyl)-N-(2-methylpropyl)aminocarbonyl,N-(1,1-dimethylethyl)-N-(1-methylethyl)aminocarbonyl,N-butyl-N-(1-methylpropyl)aminocarbonyl,N-butyl-N-(2-methylpropyl)aminocarbonyl,N-butyl-N-(1,1-dimethylethyl)aminocarbonyl,N-(1-methylpropyl)-N-(2-methylpropyl)aminocarbonyl,N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminocarbonyl orN-(1,1-dimethylethyl)-N-(2-methylpropyl)aminocarbonyl, in particularN,N-dimethylaminocarbonyl or N,N-diethylaminocarbonyl;

(C₁ -C₆ -alkyl)iminooxycarbonyl: methyliminooxycarbonyl,ethyliminooxycarbonyl, n-propyliminooxycarbonyl,1-methylethyliminooxycarbonyl, n-Butyliminooxycarbonyl,1-methylpropyliminooxycarbonyl, 2-methylpropyliminooxycarbonyl,1,1-dimethylethyliminooxycarbonyl, n-pentyliminooxycarbonyl,1-methylbutyliminooxycarbonyl, 2-methylbutyliminooxycarbonyl,3-methylbutyliminooxycarbonyl, 1,1-dimethylpropyliminooxycarbonyl,1,2-dimethylpropyliminooxycarbonyl, 2,2-dimethylpropyliminooxycarbonyl,1-ethylpropyliminooxycarbonyl, n-hexyliminooxycarbonyl,1-methylpentyliminooxycarbonyl, 2-methylpentyliminooxycarbonyl,3-methylpentyliminooxycarbonyl, 4-methylpentyliminooxycarbonyl,1,1-dimethylbutyliminooxycarbonyl, 1,2-dimethylbutyliminooxycarbonyl,1,3-dimethylbutyliminooxycarbonyl, 2,2-dimethylbutyliminooxycarbonyl,2,3-dimethylbutyliminooxycarbonyl, 3,3-dimethylbutyliminooxycarbonyl,1-ethylbutyliminooxycarbonyl, 2-ethylbutyliminooxycarbonyl,1,1,2-trimethylpropyliminooxycarbonyl,1,2,2-trimethylpropyliminooxycarbonyl,1-ethyl-1-methylpropyliminooxycarbonyl or1-ethyl-2-methylpropyliminooxycarbonyl, in particularmethyliminooxycarbonyl, ethyliminooxycarbonyl or1-methylethyliminooxycarbonyl;

C₁ -C₆ -alkylideneaminooxy: acetylideneaminooxy, 1-propylideneaminooxy,2-propylideneaminooxy, 1-butylideneaminooxy, 2-butylideneaminooxy or2-hexylideneaminooxy, in particular acetylideneaminooxy or2-propylideneaminooxy;

C₁ -C₆ -alkyliminooxy: methyliminooxy, ethyliminooxy, n-propyliminooxy,1-methylethyliminooxy, n-butyliminooxy, 1-methylpropyliminooxy,2-methylpropyliminooxy, n-pentyliminooxy, n-hexyliminooxy,1-methylpentyliminooxy, 2-methylpentyliminooxy, 3-methylpentyliminooxyor 4-methylpentyliminooxy, in particular methyliminooxy, ethyliminooxyor 1-methylethyliminooxy;

C₁ -C₆ -alkyloximino-C₁ -C₆ -alkyl: C₁ -C₆ -alkyl which is substitutedby C₁ -C₆ -alkyloximino such as methoxyimino, ethoxyimino,1-propoxyimino, 2-propoxyimino, 1-methylethoxyimino, n-butoxyimino,sec-butoxyimino, tert-butoxyimino, 1-methyl-1-propoxyimino,2-methyl-1-propoxyimino, 1-methyl-2-propoxyimino,2-methyl-2-propoxyimino, n-pentoxyimino, 2-pentoxyimino, 3-pentoxyimino,4-pentoxyimino, 1-methyl-1-butoxyimino, 2-methyl-1-butoxyimino,3-methyl-1-butoxyimino, 1-methyl-2-butoxyimino, 2-methyl-2-butoxyimino,3-methyl-2-butoxyimino, 1-methyl-3-butoxyimino, 2-methyl-3-butoxyimino,3-methyl-3-butoxyimino, 1,1-dimethyl-2-propoxyimino,1,2-dimethyl-1-propoxyimino, 1,2-dimethyl-2-propoxyimino,1-ethyl-1-propoxyimino, 1-ethyl-2-propoxyimino, n-hexoxyimino,2-hexoxyimino, 3-hexoxyimino, 4-hexoxyimino, 5-hexoxyimino,1-methyl-1-pentoxyimino, 2-methyl-1-pentoxyimino,3-methyl-1-pentoxyimino, 4-methyl-1-pentoxyimino,1-methyl-2-pentoxyimino, 2-methyl-2-pentoxyimino,3-methyl-2-pentoxyimino, 4-methyl-2-pentoxyimino,1-methyl-3-pentoxyimino, 2-methyl-3-pentoxyimino,3-methyl-3-pentoxyimino, 4-methyl-3-pentoxyimino,1-methyl-4-pentoxyimino, 2-methyl-4-pentoxyimino,3-methyl-4-pentoxyimino, 4-methyl-4-pentoxyimino,1,1-dimethyl-2-butoxyimino, 1,1-dimethyl-3-butoxyimino,1,2-dimethyl-1-butoxyimino, 1,2-dimethyl-2-butoxyimino,1,2-dimethyl-3-butoxyimino, 1,3-dimethyl-1-butoxyimino,1,3-dimethyl-2-butoxyimino, 1,3-dimethyl-3-butoxyimino,2,2-dimethyl-3-butoxyimino, 2,3-dimethyl-1-butoxyimino,2,3-dimethyl-2-butoxyimino, 2,3-dimethyl-3-butoxyimino,3,3-dimethyl-1-butoxyimino, 3,3-dimethyl-2-butoxyimino,1-ethyl-1-butoxyimino, 1-ethyl-2-butoxyimino, 1-ethyl-3-butoxyimino,2-ethyl-1-butoxyimino, 2-ethyl-2-butoxyimino, 2-ethyl-3-butoxyimino,1,1,2-trimethyl-2-propoxyimino, 1-ethyl-1-methyl-2-propoxyimino,1-ethyl-2-methyl-1-propoxyimino and 1-ethyl-2-methyl-2-propoxyimino, ie.for example methoxyiminomethyl;

C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl: C₁ -C₆ -alkyl which is substituted by C₁-C₆ -alkoxy as mentioned above, ie. for example CH₂ --OCH₃, CH₂ --OC₂H₅, n-propoxymethyl, CH₂ --OCH(CH₃)₂, n-butoxymethyl,(1-methylpropoxy)methyl, (2-methylpropoxy)methyl, CH₂ --OC(CH₃)₃,2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(n-propoxy)ethyl,2-(1-methylethoxy)ethyl, 2-(n-butoxy)ethyl, 2-(1-methylpropoxy)ethyl,2-(2-methylpropoxy)ethyl, 2-(1,1-dimethylethoxy)ethyl,2-(methoxy)propyl, 2-(ethoxy)propyl, 2-(n-propoxy)propyl,2-(1-methylethoxy)propyl, 2-(n-butoxy)propyl, 2-(1-methylpropoxy)propyl,2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl,3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(n-propoxy)propyl,3-(1-methylethoxy)propyl, 3-(n-butoxy)propyl, 3-(1-methylpropoxy)propyl,3-(2-methylpropoxy)propyl, 3-(1,1-dimethylethoxy)propyl,2-(methoxy)butyl, 2-(ethoxy)butyl, 2-(n-propoxy)butyl,2-(1-methylethoxy)butyl, 2-(n-butoxy)butyl, 2-(1-methylpropoxy)butyl,2-(2-methylpropoxy)butyl, 2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl,3-(ethoxy)butyl, 3-(n-propoxy)butyl, 3-(1-methylethoxy)butyl,3-(n-butoxy)butyl, 3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl,3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl,4-(n-propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(n-butoxy)butyl,4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl or4-(1,1-dimethylethoxy)butyl, in particular CH₂ --OCH₃ or 2-methoxyethyl;

C₁ -C₆ -alkoxy-C₁ -C₆ -alkoxy: C₁ -C₆ -alkoxy which is substituted by C₁-C₆ -alkoxy as mentioned above, ie. for example OCH₂ --OCH₃, OCH₂ --OC₂H₅, n-propoxymethoxy, OCH₂ --OCH(CH₃)₂, n-butoxymethoxy,(1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy, OCH₂ --OC(CH₃)₃,2-(methoxy)ethoxy, 2-(ethoxy)ethoxy, 2-(n-propoxy)ethoxy,2-(1-methylethoxy)ethoxy, 2-(n-butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy,2-(2-methylpropoxy)ethoxy, 2-(1,1-dimethylethoxy)ethoxy,2-(methoxy)propoxy, 2-(ethoxy)propoxy, 2-(n-propoxy)propoxy,2-(1-methylethoxy)propoxy, 2-(n-butoxy)propoxy,2-(1-methylpropoxy)propoxy, 2-(2-methylpropoxy)propoxy,2-(1,1-dimethylethoxy)propoxy, 3-(methoxy)propoxy, 3-(ethoxy)propoxy,3-(n-propoxy)propoxy, 3-(1-methylethoxy)propoxy, 3-(n-butoxy)propoxy,3-(1-methylpropoxy)propoxy, 3-(2-methylpropoxy)propoxy,3-(1,1-dimethylethoxy)propoxy, 2-(methoxy)butoxy, 2-(ethoxy)butoxy,2-(n-propoxy)butoxy, 2-(1-methylethoxy)butoxy, 2-(n-butoxy)butoxy,2-(1-methylpropoxy)butoxy, 2-(2-methylpropoxy)butoxy,2-(1,1-dimethylethoxy)butoxy, 3-(methoxy)butoxy, 3-(ethoxy)butoxy,3-(n-propoxy)butoxy, 3-(1-methylethoxy)butoxy, 3-(n-butoxy)butoxy,3-(1-methylpropoxy)butoxy, 3-(2-methylpropoxy)butoxy,3-(1,1-dimethylethoxy)butoxy, 4-(methoxy)butoxy, 4-(ethoxy)butoxy,4-(n-propoxy)butoxy, 4-(1-methylethoxy)butoxy, 4-(n-butoxy)butoxy,4-(1-methylpropoxy)butoxy, 4-(2-methylpropoxy)butoxy,4-(1,1-dimethylethoxy)butoxy, 5-(methoxy)pentoxy, 5-(ethoxy)pentoxy,5-(n-propoxy)pentoxy, 5-(1-methylethoxy)pentoxy, 5-(n-butoxy)pentoxy,5-(1-methylpropoxy)pentoxy, 5-(2-methylpropoxy)pentoxy,5-(1,1-dimethylethoxy)pentoxy, 6-(methoxy)hexoxy, 6-(ethoxy)hexoxy,6-(n-propoxy)hexoxy, 6-(1-methylethoxy)hexoxy, 6-(n-butoxy)hexoxy,6-(1-methylpropoxy)hexoxy, 6-(2-methylpropoxy)hexoxy or6-(1,1-dimethylethoxy)hexoxy, in particular OCH₂ --OCH₃ or OCH₂ --OC₂ H₅;

(C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkoxy: C₁ -C₆ -alkoxy which issubstituted by (C₁ -C₆ -alkoxy)carbonyl as mentioned above, ie. forexample OCH₂ --CO--OCH₃, OCH₂ --CO--OC₂ H₅, OCH₂ --CO--OCH₂ --C₂ H₅,OCH₂ --CO--OCH(CH₃)₂, n-butoxycarbonylmethoxy,1-(methoxycarbonyl)ethoxy, 2-(methoxycarbonyl)ethoxy,2-(ethoxycarbonyl)ethoxy, 2-(n-propoxycarbonyl)ethoxy,2-(n-butoxycarbonyl)ethoxy, 3-(methoxycarbonyl)propoxy,3-(ethoxycarbonyl)propoxy, 3-(n-propoxycarbonyl)propoxy,3-(n-butoxycarbonyl)propoxy, 4-(methoxycarbonyl)butoxy,4-(ethoxycarbonyl)butoxy, 4-(n-propoxycarbonyl)butoxy,4-(n-butoxycarbonyl)butoxy, 5-(methoxycarbonyl)pentoxy,5-(ethoxycarbonyl)pentoxy, 5-(n-propoxycarbonyl)pentoxy,5-(n-butoxycarbonyl)butoxy, 6-(methoxycarbonyl)hexoxy,6-(ethoxycarbonyl)hexoxy, 6-(n-propoxycarbonyl)hexoxy or6-(n-butoxycarbonyl)hexoxy, in particular OCH₂ --CO--OCH₃ or1-(methoxycarbonyl)ethoxy;

(C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkyl: C₁ -C₆ -alkyl which issubstituted by (C₁ -C₆ -alkoxy)carbonyl as mentioned above, ie. forexample methoxycarbonylmethyl, ethoxycarbonylmethyl,1-(methoxycarbonyl)ethyl, 2-(methoxycarbonyl)ethyl,2-(ethoxycarbonyl)ethyl, 3-(methoxycarbonyl)propyl,4-(methoxycarbonyl)butyl, 5-(methoxycarbonyl)pentyl or6-(methoxycarbonyl)hexyl;

(C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkylsulfonyl: C₁ -C₆ -alkylsulfonylwhich is substituted by (C₁ -C₆ -alkoxy)carbonyl as mentioned above, ie.for example methoxycarbonylmethylsulfonyl, ethoxycarbonylmethylsulfonyl,1-(methoxycarbonyl)ethylsulfonyl, 2-(methoxycarbonyl)ethylsulfonyl,2-(ethoxycarbonyl)ethylsulfonyl, 3-(methoxycarbonyl)propylsulfonyl,4-(methoxycarbonyl)butylsulfonyl, 5-(methoxycarbonyl)pentylsulfonyl or6-(methoxycarbonyl)hexylsulfonyl;

C₁ -C₆ -alkylthio-C₁ -C₆ -alkyl: C₁ -C₆ -alkyl which is substituted byC₁ -C₆ -alkylthio as mentioned above, ie. for example CH₂ --SCH₃, CH₂--SC₂ H₅, n-propylthiomethyl, CH₂ --SCH(CH₃)₂, n-butylthiomethyl,(1-methylpropylthio)methyl, CH₂ --SCH₂ --CH(CH₃)₂, CH₂ --SC(CH₃)₃,2-methylthioethyl, 2-ethylthioethyl, 2-(n-propylthio)ethyl,2-(1-methylethylthio)ethyl, 2-(n-butylthio)ethyl,2-(1-methylpropylthio)ethyl, 2-(2-methylpropylthio)ethyl,2-(1,1-dimethylethylthio)ethyl, 2-(methylthio)propyl,3-(methylthio)propyl, 2-(ethylthio)propyl, 3-(ethylthio)propyl,3-(propylthio)propyl, 3-(butylthio)propyl, 4-(methylthio)butyl,4-(ethylthio)butyl, 4-(n-propylthio)butyl or 4-(n-butylthio)butyl, inparticular 2-(methylthio)ethyl;

C₁ -C₆ -alkylthio-(C₁ -C₆ -alkyl)carbonyl: (C₁ -C₆ -alkyl)carbonyl whichis substituted by C₁ -C₆ -alkylthio as mentioned above, preferably bySCH₃ or SC₂ H₅, ie. for example methylthiomethylcarbonyl,ethylthiomethylcarbonyl, 1-(methylthio)ethylcarbonyl,2-(methylthio)ethylcarbonyl, 3-(methylthio)propylcarbonyl,4-(methylthio)butylcarbonyl, 5-(methylthio)pentylcarbonyl or6-(methylthio)hexylcarbonyl, in particular CO--CH₂ --SCH₃ orCO--CH(CH₃)--SCH₃ ;

di(C₁ -C₆ -alkyl)amino-C₁ -C₆ -alkoxy: C₁ -C₆ -alkoxy which issubstituted by di(C₁ -C₆ -alkyl)amino such as N(CH₃)₂, N(C₂ H₅)₂,N,N-dipropylamino, N,N-di(1-methylethyl)amino, N,N-dibutylamino,N,N-di(1-methylpropyl)amino, N,N-di(2-methylpropyl)amino, N[C(CH₃)₃ ]₂,N-ethyl-N-methylamino, N-methyl-N-propylamino,N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino,N-methyl-N-(1-methylpropyl)amino, N-methyl-N-(2-methylpropyl)amino,N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino,N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino,N-ethyl-N-1-methylpropyl)amino, N-ethyl-N-(2-methylpropyl)amino,N-ethyl-N-(1,1-dimethylethyl)amino, N-(1-methylethyl)-N-propylamino,N-butyl-N-propylamino, N-(1-methylpropyl)-N-propylamino,N-(2-methylpropyl)-N-propylamino, N-(1,1-dimethylethyl)-N-propylamino,N-butyl-N-(1-methylethyl)amino,N-(1-methylethyl)-N-(1-methylpropyl)amino,N-(1-methylethyl)-N-(2-methylpropyl)amino,N-(1,1-dimethylethyl)-N-(1-methylethyl)amino,N-butyl-N-(1-methylpropyl)amino, N-butyl-N-(2-methylpropyl)amino,N-butyl-N-(1,1-dimethylethyl)amino,N-(1-methylpropyl)-N-(2-methylpropyl)amino,N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino orN-(1,1-dimethylethyl)-N-(2-methylpropyl)amino, preferably byN,N-dimethylamino or N,N-diethylamino, ie. for example OCH₂ --N(CH₃)₂,OCH₂ --N(C₂ H₅)₂, OCH(CH₃)--N(CH₃)₂, 2-(dimethylamino)ethoxy,OCH(CH₃)--N(C₂ H₅)₂, 3-(dimethylamino)propoxy, 4-(dimethylamino)butoxy,5-(dimethylamino)pentoxy or 6-(dimethylamino)hexoxy, in particular OCH₂--N(CH₃)₂ or OCH(CH₃)--N(CH₃)₂ ;

C₃ -C₆ -alkenyl: for example prop-2-en-1-yl, n-buten-4-yl,1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, 2-buten-1-yl,n-penten-3-yl, n-penten-4-yl, 1-methylbut-2-en-1-yl,2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl,2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl,1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-2-en-1-yl,1-ethylprop-2-en-1-yl, n-hex-3-en-1-yl, n-hex-4-en-1-yl,n-hex-5-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl,3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl,2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl,1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl,1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl,1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl,2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-2-en-1-yl,2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-2-en-1-yl,1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-2-en-1-yl,2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl,1-ethyl-1-methylprop-2-en-1-yl or 1-ethyl-2-methylprop-2-en-1-yl, inparticular prop-2-en-1-yl or n-buten-4-yl;

C₂ -C₆ -alkenyl: ethenyl or one of the radicals mentioned under C₃ -C₆-alkenyl, in particular ethenyl or prop-2-en-1-yl;

C₃ -C₆ -haloalkenyl: C₃ -C₆ -alkenyl as mentioned above which ispartially or fully substituted by fluorine, chlorine and/or bromine, ie.for example 2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl,3,3-dichloroallyl, 2,3,3-trichloroallyl, 2,3-dichlorobut-2-enyl,2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl,2,3,3-tribromoallyl or 2,3-dibromobut-2-enyl, in particular2-chloroallyl or 3,3-dichloroallyl;

phenyl-C₃ -C₆ -alkenyloxy: for example 3-phenylallyloxy,4-phenylbut-2-enyloxy, 4-phenylbut-3-enyloxy or 5-phenylpent-4-enyloxy,preferably 3-phenylallyloxy or 4-phenylbut-2-enyloxy, in particular3-phenylallyloxy;

heterocyclyl-C₃ -C₆ -alkenyloxy: for example 3-heterocyclylallyloxy,4-heterocyclylbut-2-enyloxy, 4-heterocyclylbut-3-enyloxy or5-heterocyclylpent-4-enyloxy, preferably 3-heterocyclylallyloxy or4-heterocyclylbut-2-enyloxy, in particular 3-heterocyclylallyloxy;

C₃ -C₆ -alkenyloxy: prop-1-en-1-yloxy, prop-2-en-1-yloxy,1-methylethenyloxy, n-buten-1-yloxy, n-buten-2-yloxy, n-buten-3-yloxy,1-methylprop-1-en-1-yloxy, 2-methylprop-1-en-1-yloxy,1-methyl-prop-2-en-1-yloxy, 2-methylprop-2-en-1-yloxy, n-penten-1-yloxy,n-penten-2-yloxy, n-penten-3-yloxy, n-penten-4-yloxy,1-methylbut-1-en-1-yloxy, 2-methylbut-1-en-1-yloxy,3-methylbut-1-en-1-yloxy, 1-methylbut-2-en-1-yloxy,2-methylbut-2-en-1-yloxy, 3-methylbut-2-en-1-yloxy,1-methylbut-3-en-1-yloxy, 2-methylbut-3-en-1-yloxy,3-methylbut-3-en-1-yloxy, 1,1-dimethylprop-2-en-1-yloxy,1,2-dimethylprop-1-en-1-yloxy, 1,2-dimethylprop-2-en-1-yloxy,1-ethylprop-1-en-2-yloxy, 1-ethylprop-2-en-1-yloxy, n-hex-1-en-1-yloxy,n-hex-2-en-1-yloxy, n-hex-3-en-1-yloxy, n-hex-4-en-1-yloxy,n-hex-5-en-1-yloxy, 1-methylpent-1-en-1-yloxy,2-methylpent-1-en-1-yloxy, 3-methylpent-1-en-1-yloxy,4-methylpent-1-en-1-yloxy, 1-methylpent-2-en-1-yloxy,2-methylpent-2-en-1-yloxy, 3-methylpent-2-en-1-yloxy,4-methylpent-2-en-1-yloxy, 1-methylpent-3-en-1-yloxy,2-methylpent-3-en-1-yloxy, 3-methylpent-3-en-1-yloxy,4-methylpent-3-en-1-yloxy, 1-methylpent-4-en-1-yloxy,2-methylpent-4-en-1-yloxy, 3-methylpent-4-en-1-yloxy,4-methylpent-4-en-1-yloxy, 1,1-dimethylbut-2-en-1-yloxy,1,1-dimethylbut-3-en-1-yloxy, 1,2-dimethylbut-1-en-1-yloxy,1,2-dimethylbut-2-en-1-yloxy, 1,2-dimethylbut-3-en-1-yloxy,1,3-dimethylbut-1-en-1-yloxy, 1,3-dimethylbut-2-en-1-yloxy,1,3-dimethylbut-3-en-1-yloxy, 2,2-dimethylbut-3-en-1-yloxy,2,3-dimethylbut-1-en-1-yloxy, 2,3-dimethylbut-2-en-1-yloxy,2,3-dimethylbut-3-en-1-yloxy, 3,3-dimethylbut-1-en-1-yloxy,3,3-dimethylbut-2-en-1-yloxy, 1-ethylbut-1-en-1-yloxy,1-ethylbut-2-en-1-yloxy, 1-ethylbut-3-en-1-yloxy,2-ethylbut-1-en-1-yloxy, 2-ethylbut-2-en-1-yloxy,2-ethylbut-3-en-1-yloxy, 1,1,2-trim, 2-eprop-2-en-1-yloxy,1-ethyl-1-methylprop-2-en-1-yloxy, 1-ethyl-2-methylprop-1-en-1-yloxy or1-ethyl-2-methylprop-2-en-1-yloxy, in particular prop-2-en-1-yloxy;

C₂ -C₆ -alkenyloxy: ethenyloxy or one of the radicals mentioned under C₃-C₆ -alkenyloxy, in particular ethenyloxy or prop-2 -en-1 -yloxy;

C₃ -C₆ -haloalkenyloxy: C₃ -C₆ -alkenyloxy as mentioned above which ispartially or fully substituted by fluorine, chlorine and/or bromine, ie.for example 2-chloroallyloxy, 3-chloroallyloxy, 2,3-dichloroallyloxy,3,3-dichloroallyloxy, 2,3,3-trichloroallyloxy,2,3-dichlorobut-2-enyloxy, 2-bromoallyloxy, 3-bromoallyloxy,2,3-dibromoallyloxy, 3,3-dibromoallyloxy, 2,3,3-tribromoallyloxy or2,3-dibromobut-2-enyloxy, in particular 2-chloroallyloxy or3,3-dichloroallyloxy;

C₃ -C₆ -alkenylthio: prop-1-en-1-ylthio, prop-2-en-1-ylthio,1-methylethenylthio, n-buten-1-ylthio, n-buten-2-ylthio,n-buten-3-ylthio, 1-methylprop-1-en-1-ylthio,2-methylprop-1-en-1-ylthio, 1-methylprop-2-en-1-ylthio,2-methylprop-2-en-1-ylthio, n-penten-1-ylthio, n-penten-2-ylthio,n-penten-3-ylthio, n-penten-4-ylthio, 1-methylbut-1-en-1-ylthio,2-methylbut-1-en-1-ylthio, 3-methylbut-1-en-1-ylthio,1-methylbut-2-en-1-ylthio, 2-methylbut-2-en-1-ylthio,3-methylbut-2-en-1-ylthio, 1-methylbut-3-en-1-ylthio,2-methylbut-3-en-1-ylthio, 3-methylbut-3-en-1-ylthio,1,1-dimethylprop-2-en-1-ylthio, 1,2-dimethylprop-1-en-1-ylthio,1,2-dimethylprop-2-en-1-ylthio, 1-ethylprop-1-en-2-ylthio,1-ethylprop-2-en-1-ylthio, n-hex-1-en-1-ylthio, n-hex-2-en-1-ylthio,n-hex-3-en-1-ylthio, n-hex-4-en-1-ylthio, n-hex-5-en-1-ylthio,1-methylpent-1-en-1-ylthio, 2-methylpent-1-en-1-ylthio,3-methylpent-1-en-1-ylthio, 4-methylpent-1-en-1-ylthio,1-methylpent-2-en-1-ylthio, 2-methylpent-2-en-1-ylthio,3-methylpent-2-en-1-ylthio, 4-methylpent-2-en-1-ylthio,1-methylpent-3-en-1-ylthio, 2-methylpent-3-en-1-ylthio,3-methylpent-3-en-1-ylthio, 4-methylpent-3-en-1-ylthio,1-methylpent-4-en-1-ylthio, 2-methylpent-4-en-1-ylthio,3-methylpent-4-en-1-ylthio, 4-methylpent-4-en-1-ylthio,1,1-dimethylbut-2-en-1-ylthio, 1,1-dimethylbut-3-en-1-ylthio,1,2-dimethylbut-1-en-1-ylthio, 1,2-dimethylbut-2-en-1-ylthio,1,2-dimethylbut-3-en-1-ylthio, 1,3-dimethylbut-1-en-1-ylthio,1,3-dimethylbut-2-en-1-ylthio, 1,3-dimethylbut-3-en-1-ylthio,2,2-dimethylbut-3-en-1-ylthio, 2,3-dimethylbut-1-en-1-ylthio,2,3-dimethylbut-2-en-1-ylthio, 2,3-dimethylbut-3-en-1-ylthio,3,3-dimethylbut-1-en-1-ylthio, 3,3-dimethylbut-2-en-1-ylthio,1-ethylbut-1-en-1-ylthio, 1-ethylbut-2-en-1-ylthio,1-ethylbut-3-en-1-ylthio, 2-ethylbut-1-en-1-ylthio,2-ethylbut-2-en-1-ylthio, 2-ethylbut-3-en-1-ylthio,1,1,2-trimethylprop-2-en-1-ylthio, 1-ethyl-1-methylprop-2-en-1-ylthio,1-ethyl-2-methylprop-1-en-1-ylthio or1-ethyl-2-methylprop-2-en-1-ylthio, in particular prop-2-en-1-ylthio;

C₂ -C₆ -alkenylthio: ethenylthio or one of the radicals mentioned underC₃ -C₆ -alkenylthio, in particular ethenylthio or prop-2-en-1-ylthio;

C₃ -C₆ -alkynyl: prop-1-yn-1-yl, prop-2-yn-1-yl, n-but-1-yn-1-yl,n-but-1-yn-3-yl, n-but-1-yn-4-yl, n-but-2-yn-1-yl, n-pent-1-yn-1-yl,n-pent-1-yn-3-yl, n-pent-1-yn-4-yl, n-pent-1-yn-5-yl, n-pent-2-yn-1-yl,n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl,3-methylbut-1-yn-4-yl, n-hex-1-yn-1-yl, n-hex-1-yn-3-yl,n-hex-1-yn-4-yl, n-hex-1-yn-5-yl, n-hex-1-yn-6-yl, n-hex-2-yn-1-yl,n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-yn-1-yl,n-hex-3-yn-2-yl, 3-methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl,3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-1-yn-1-yl,4-methylpent-2-yn-4-yl or 4-methylpent-2-yn-5-yl, in particularprop-2-yn-1-yl;

C₂ -C₆ -alkynyl: ethynyl or one of the radicals mentioned under C₃ -C₆-alkynyl, in particular ethynyl or prop-2-yn-1-yl;

C₃ -C₆ -alkynyloxy: prop-1-yn-1-yloxy, prop-2-yn-1-yloxy,n-but-1-yn-1-yloxy, n-but-1-yn-3-yloxy, n-but-1-yn-4-yloxy,n-but-2-yn-1-yloxy, n-pent-1-yn-1-yloxy, n-pent-1-yn-3-yloxy,n-pent-1-yn-4-yloxy, n-pent-1-yn-5-yloxy, n-pent-2-yn-1-yloxy,n-pent-2-yn-4-yloxy, n-pent-2-yn-5-yloxy, 3-methylbut-1-yn-3-yloxy,3-methylbut-1-yn-4-yloxy, n-hex-1-yn-1-yloxy, n-hex-1-yn-3-yloxy,n-hex-1-yn-4-yloxy, n-hex-1-yn-5-yloxy, n-hex-1-yn-6-yloxy,n-hex-2-yn-1-yloxy, n-hex-2-yn-4-yloxy, n-hex-2-yn-5-yloxy,n-hex-2-yn-6-yloxy, n-hex-3-yn-1-yloxy, n-hex-3-yn-2-yloxy,3-methylpent-1-yn-1-yloxy, 3-methylpent-1-yn-3-yloxy,3-methylpent-1-yn-4-yloxy, 3-methylpent-1-yn-5-yloxy,4-methylpent-1-yn-1-yloxy, 4-methylpent-2-yn-4-yloxy or4-methylpent-2-yn-5-yloxy, in particular prop-2-yn-1-yloxy;

C₂ -C₆ -alkynyloxy: ethynyloxy or one of the radicals mentioned under C₃-C₆ -alkynyloxy, in particular ethynyloxy or prop-2-yn-1-yloxy;

C₃ -C₆ -alkynylthio: prop-1-yn-1-ylthio, prop-2-yn-1-ylthio,n-but-1-yn-1-ylthio, n-but-1-yn-3-ylthio, n-but-1-yn-4-ylthio,n-but-2-yn-1-ylthio, n-pent-1-yn-1-ylthio, n-pent-1-yn-3-ylthio,n-pent-1-yn-4-ylthio, n-pent-1-yn-5-ylthio, n-pent-2-yn-1-ylthio,n-pent-2-yn-4-ylthio, n-pent-2-yn-5-ylthio, 3-methylbut-1-yn-3-ylthio,3-methylbut-1-yn-4-ylthio, n-hex-1-yn-1-ylthio, n-hex-1-yn-3-ylthio,n-hex-1-yn-4-ylthio, n-hex-1-yn-5-ylthio, n-hex-1-yn-6-ylthio,n-hex-2-yn-1-ylthio, n-hex-2-yn-4-ylthio, n-hex-2-yn-5-ylthio,n-hex-2-yn-6-ylthio, n-hex-3-yn-1-ylthio, n-hex-3-yn-2-ylthio,3-methylpent-1-yn-1-ylthio, 3-methylpent-1-yn-3-ylthio,3-methylpent-1-yn-4-ylthio, 3-methylpent-1-yn-5-ylthio,4-methylpent-1-yn-1-ylthio, 4-methylpent-2-yn-4-ylthio or4-methylpent-2-yn-5-ylthio, in particular prop-2-yn-1-ylthio;

C₂ -C₆ -alkynylthio: ethynylthio or one of the radicals mentioned underC₃ -C₆ -alkynylthio, in particular ethynylthio or prop-2-yn-1-ylthio;

(C₃ -C₆ -alkenyl)oxycarbonyl: prop-1-en-1-yloxycarbonyl,prop-2-en-1-yloxycarbonyl, 1-methylethenyloxycarbonyl,n-buten-1-yloxycarbonyl, n-buten-2-yloxycarbonyl,n-buten-3-yloxycarbonyl, 1-methylprop-1-en-1-yloxycarbonyl,2-methylprop-1-en-1-yloxycarbonyl, 1-methylprop-2-en-1-yloxycarbonyl,2-methylprop-2-en-1-yloxycarbonyl, n-penten-1-yloxycarbonyl,n-penten-2-yloxycarbonyl, n-penten-3-yloxycarbonyl,n-penten-4-yloxycarbonyl, 1-methylbut-1-en-1-yloxycarbonyl,2-methylbut-1-en-1-yloxycarbonyl, 3-methylbut-1-en-1-yloxycarbonyl,1-methylbut-2-en-1-yloxycarbonyl, 2-methylbut-2-en-1-yloxycarbonyl,3-methylbut-2-en-1-yloxycarbonyl, 1-methylbut-3-en-1-yloxycarbonyl,2-methylbut-3-en-1-yloxycarbonyl, 3-methylbut-3-en-1-yloxycarbonyl,1,1-dimethylprop-2-en-1-yloxycarbonyl,1,2-dimethylprop-1-en-1-yloxycarbonyl,1,2-dimethylprop-2-en-1-yloxycarbonyl, 1-ethylprop-1-en-2-yloxycarbonyl,1-ethylprop-2-en-1-yloxycarbonyl, n-hex-1-en-1-yloxycarbonyl,n-hex-2-en-1-yloxycarbonyl, n-hex-3-en-1-yloxycarbonyl,n-hex-4-en-1-yloxycarbonyl, n-hex-5-en-1-yloxycarbonyl,1-methylpent-1-en-1-yloxycarbonyl, 2-methylpent-1-en-1-yloxycarbonyl,3-methylpent-1-en-1-yloxycarbonyl, 4-methylpent-1-en-1-yloxycarbonyl,1-methylpent-2-en-1-yloxycarbonyl, 2-methylpent-2-en-1-yloxycarbonyl,3-methylpent-2-en-1-yloxycarbonyl, 4-methylpent-2-en-1-yloxycarbonyl,1-methylpent-3-en-1-yloxycarbonyl, 2-methylpent-3-en-1-yloxycarbonyl,3-methylpent-3-en-1-yloxycarbonyl, 4-methylpent-3-en-1-yloxycarbonyl,1-methylpent-4-en-1-yloxycarbonyl, 2-methylpent-4-en-1-yloxycarbonyl,3-methylpent-4-en-1-yloxycarbonyl, 4-methylpent-4-en-1-yloxycarbonyl,1,1-dimethylbut-2-en-1-yloxycarbonyl,1,1-dimethylbut-3-en-1-yloxycarbonyl,1,2-dimethylbut-1-en-1-yloxycarbonyl,1,2-dimethylbut-2-en-1-yloxycarbonyl,1,2-dimethylbut-3-en-1-yloxycarbonyl,1,3-dimethylbut-1-en-1-yloxycarbonyl,1,3-dimethylbut-2-en-1-yloxycarbonyl,1,3-dimethylbut-3-en-1-yloxycarbonyl,2,2-dimethylbut-3-en-1-yloxycarbonyl,2,3-dimethylbut-1-en-1-yloxycarbonyl,2,3-dimethylbut-2-en-1-yloxycarbonyl,2,3-dimethylbut-3-en-1-yloxycarbonyl,3,3-dimethylbut-1-en-1-yloxycarbonyl,3,3-dimethylbut-2-en-1-yloxycarbonyl, 1-tethylbut-1-en-1-yloxycarbonyl,1-ethylbut-2-en-1-yloxycarbonyl, 1-ethylbut-3-en-1-yloxycarbonyl,2-ethylbut-1-en-1-yloxycarbonyl, 2-ethylbut-2-en-1-yloxycarbonyl,2-ethylbut-3-en-1-yloxycarbonyl,1,1,2-trimethylprop-2-en-1-yloxycarbonyl,1-ethyl-1-methylprop-2-en-1-yloxycarbonyl,1-ethyl-2-methylprop-1-en-1-yloxycarbonyl or1-ethyl-2-methylprop-2-en-1-yloxycarbonyl, in particularprop-2-en-1-yloxycarbonyl;

(C₃ -C₆ -alkenyloxy)carbonyl-C₁ -C₆ -alkyl: C₁ -C₆ -alkyl which issubstituted by (C₃ -C₆ -alkenyloxy)carbonyl as mentioned above,preferably by prop-2-en-1-yloxycarbonyl, ie. for exampleprop-2-en-1-yloxycarbonylmethyl;

(C₃ -C₆ -alkenyl)carbonyloxy: prop-1-en-1-ylcarbonyloxy,prop-2-en-1-ylcarbonyloxy, 1-methylethenylcarbonyloxy,n-buten-1-ylcarbonyloxy, n-buten-2-ylcarbonyloxy,n-buten-3-ylcarbonyloxy, 1-methylprop-1-en-1-ylcarbonyloxy,2-methylprop-1-en-1-ylcarbonyloxy, 1-methylprop-2-en-1-ylcarbonyloxy,2-methylprop-2-en-1-ylcarbonyloxy, n-penten-1-ylcarbonyloxy,n-penten-2-ylcarbonyloxy, n-penten-3-ylcarbonyloxy,n-penten-4-ylcarbonyloxy, 1-methylbut-1-en-1-ylcarbonyloxy,2-methylbut-1-en-1-ylcarbonyloxy, 3-methylbut-1-en-1-ylcarbonyloxy,1-methylbut-2-en-1-ylcarbonyloxy, 2-methylbut-2-en-1-ylcarbonyloxy,3-methylbut-2-en-1-ylcarbonyloxy, 1-methylbut-3-en-1-ylcarbonyloxy,2-methylbut-3-en-1-ylcarbonyloxy, 3-methylbut-3-en-1-ylcarbonyloxy,1,1-dimethylprop-2-en-1-ylcarbonyloxy,1,2-dimethylprop-1-en-1-ylcarbonyloxy,1,2-dimethylprop-2-en-1-ylcarbonyloxy, 1-ethylprop-1-en-2-ylcarbonyloxy,1-ethylprop-2-en-1-ylcarbonyloxy, n-hex-1-en-1-ylcarbonyloxy,n-hex-2-en-1-ylcarbonyloxy, n-hex-3-en-1-ylcarbonyloxy,n-hex-4-en-1-ylcarbonyloxy, n-hex-5-en-1-ylcarbonyloxy,1-methylpent-1-en-1-ylcarbonyloxy, 2-methylpent-1-en-1-ylcarbonyloxy,3-methylpent-1-en-1-ylcarbonyloxy, 4-methylpent-1-en-1-ylcarbonyloxy,1-methylpent-2-en-1-ylcarbonyloxy, 2-methylpent-2-en-1-ylcarbonyloxy,3-methylpent-2-en-1-ylcarbonyloxy, 4-methylpent-2-en-1-ylcarbonyloxy,1-methylpent-3-en-1-ylcarbonyloxy, 2-methylpent-3-en-1-ylcarbonyloxy,3-methylpent-3-en-1-ylcarbonyloxy, 4-methylpent-3-en-1-ylcarbonyloxy,1-methylpent-4-en-1-ylcarbonyloxy, 2-methylpent-4-en-1-ylcarbonyloxy,3-methylpent-4-en-1-ylcarbonyloxy, 4-methylpent-4-en-1-ylcarbonyloxy,1,1-dimethylbut-2-en-1-ylcarbonyloxy,1,1-dimethylbut-3-en-1-ylcarbonyloxy,1,2-dimethylbut-1-en-1-ylcarbonyloxy,1,2-dimethylbut-2-en-1-ylcarbonyloxy,1,2-dimethylbut-3-en-1-ylcarbonyloxy,1,3-dimethylbut-1-en-1-ylcarbonyloxy,1,3-dimethylbut-2-en-1-ylcarbonyloxy,1,3-dimethylbut-3-en-1-ylcarbonyloxy,2,2-dimethylbut-3-en-1-ylcarbonyloxy,2,3-dimethylbut-1-en-1-ylcarbonyloxy,2,3-dimethylbut-2-en-1-ylcarbonyloxy,2,3-dimethylbut-3-en-1-ylcarbonyloxy,3,3-dimethylbut-1-en-1-ylcarbonyloxy,3,3-dimethylbut-2-en-1-ylcarbonyloxy, 1-ethylbut-1-en-1-ylcarbonyloxy,1-ethylbut-2-en-1-ylcarbonyloxy, 1-ethylbut-3-en-1-ylcarbonyloxy,2-ethylbut-1-en-1-ylcarbonyloxy, 2-ethylbut-2-en-1-ylcarbonyloxy,2-ethylbut-3-en-1-ylcarbonyloxy,1,1,2-trimethylprop-2-en-1-ylcarbonyloxy,1-ethyl-1-methylprop-2-en-1-ylcarbonyloxy,1-ethyl-2-methylprop-1-en-1-ylcarbonyloxy or1-ethyl-2-methylprop-2-en-1-ylcarbonyloxy, in particularprop-2-en-1-ylcarbonyloxy;

(C₂ -C₆ -alkenyl)carbonyloxy: ethenylcarbonyloxy or one of the radicalsmentioned under (C₃ -C₆ -alkenyl)carbonyloxy, in particularethenylcarbonyloxy or prop-2-en-1-ylcarbonyloxy;

(C₃ -C₆ -alkenyl)carbonylthio: prop-1-en-1-ylcarbonylthio,prop-2-en-1-ylcarbonylthio, 1-methylethenylcarbonylthio,n-buten-1-ylcarbonylthio, n-buten-2-ylcarbonylthio,n-buten-3-ylcarbonylthio, 1-methylprop-1-en-1-ylcarbonylthio,2-methylprop-1-en-1-ylcarbonylthio, 1-methylprop-2-en-1-ylcarbonylthio,2-methylprop-2-en-1-ylcarbonylthio, n-penten-1-ylcarbonylthio,n-penten-2-ylcarbonylthio, n-penten-3-ylcarbonylthio,n-penten-4-ylcarbonylthio, 1-methylbut-1-en-1-ylcarbonylthio,2-methylbut-1-en-1-ylcarbonylthio, 3-methylbut-1-en-1-ylcarbonylthio,1-methylbut-2-en-1-ylcarbonylthio, 2-methylbut-2-en-1-ylcarbonylthio,3-methylbut-2-en-1-ylcarbonylthio, 1-methylbut-3-en-1-ylcarbonylthio,2-methylbut-3-en-1-ylcarbonylthio, 3-methylbut-3-en-1-ylcarbonylthio,1,1-dimethylprop-2-en-1-ylcarbonylthio,1,2-dimethylprop-1-en-1-ylcarbonylthio,1,2-dimethylprop-2-en-1-ylcarbonylthio,1-ethylprop-1-en-2-ylcarbonylthio, 1-ethylprop-2-en-1-ylcarbonylthio,n-hex-1-en-1-ylcarbonylthio, n-hex-2-en-1-ylcarbonylthio,n-hex-3-en-1-ylcarbonylthio, n-hex-4-en-1-ylcarbonylthio,n-hex-5-en-1-ylcarbonylthio, 1-methylpent-1-en-1-ylcarbonylthio,2-methylpent-1-en-1-ylcarbonylthio, 3-methylpent-1-en-1-ylcarbonylthio,4-methylpent-1-en-1-ylcarbonylthio, 1-methylpent-2-en-1-ylcarbonylthio,2-methylpent-2-en-1-ylcarbonylthio, 3-methylpent-2-en-1-ylcarbonylthio,4-methylpent-2-en-1-ylcarbonylthio, 1-methylpent-3-en-1-ylcarbonylthio,2-methylpent-3-en-1-ylcarbonylthio, 3-methylpent-3-en-1-ylcarbonylthio,4-methylpent-3-en-1-ylcarbonylthio, 1-methylpent-4-en-1-ylcarbonylthio,2-methylpent-4-en-1-ylcarbonylthio, 3-methylpent-4-en-1-ylcarbonylthio,4-methylpent-4-en-1-ylcarbonylthio,1,1-dimethylbut-2-en-1-ylcarbonylthio,1,1-dimethylbut-3-en-1-ylcarbonylthio,1,2-dimethylbut-2-en-1-ylcarbonylthio,1,2-dimethylbut-2-en-1-ylcarbonylthio,1,2-dimethylbut-1-en-1-ylcarbonylthio,1,3-dimethylbut-1-en-1-ylcarbonylthio,1,3-dimethylbut-2-en-1-ylcarbonylthio,1,3-dimethylbut-3-en-1-ylcarbonylthio,2,3-dimethylbut-3-en-1-ylcarbonylthio,2,3-dimethylbut-2-en-1-ylcarbonylthio,2,3-dimethylbut-3-en-1-ylcarbonylthio,2,3-dimethylbut-1-en-1-ylcarbonylthio,3,3-dimethylbut-2-en-1-ylcarbonylthio,3,3-dimethylbut-1-en-1-ylcarbonylthio, 1-ethylbut-2-en-1-ylcarbonylthio,1-ethylbut-3-en-1-ylcarbonylthio, 1-ethylbut-3-en-1-ylcarbonylthio,2-ethylbut-2-en-1-ylcarbonylthio, 2-ethylbut-3-en-1-ylcarbonylthio,2-ethylbut-3-en-1-ylcarbonylthio,1,1,2-trimethylprop-2-en-1-ylcarbonylthio,1-ethyl-1-methylprop-2-en-1-ylcarbonylthio,1-ethyl-2-methylprop-1-en-1-ylcarbonylthio or1-ethyl-2-methylprop-2-en-1-ylcarbonylthio, in particularprop-2-en-1-yl-carbonylthio;

(C₂ -C₆ -alkenyl)carbonylthio: ethenylcarbonylthio or one of theradicals mentioned under (C₃ -C₆ -alkenyl)carbonylthio, in particularprop-2-en-1-ylcarbonylthio;

(C₃ -C₆ -alkynyl)carbonyloxy: prop-1-yn-1-ylcarbonyloxy,prop-2-yn-1-ylcarbonyloxy, n-but-1-yn-1-ylcarbonyloxy,n-but-1-yn-3-ylcarbonyloxy, n-but-1-yn-4-ylcarbonyloxy,n-but-2-yn-1-ylcarbonyloxy, n-pent-1-yn-1-ylcarbonyloxy,n-pent-1-yn-3-ylcarbonyloxy, n-pent-1-yn-4-ylcarbonyloxy,n-pent-1-yn-5-ylcarbonyloxy, n-pent-2-yn-1-ylcarbonyloxy,n-pent-2-yn-4-ylcarbonyloxy, n-pent-2-yn-5-ylcarbonyloxy,3-methylbut-1-yn-3-ylcarbonyloxy, 3-methylbut-1-yn-4-ylcarbonyloxy,n-hex-1-yn-1-ylcarbonyloxy, n-hex-1-yn-3-ylcarbonyloxy,n-hex-1-yn-4-ylcarbonyloxy, n-hex-1-yn-5-ylcarbonyloxy,n-hex-1-yn-6-ylcarbonyloxy, n-hex-2-yn-1-ylcarbonyloxy,n-hex-2-yn-4-ylcarbonyloxy, n-hex-2-yn-5-ylcarbonyloxy,n-hex-2-yn-6-ylcarbonyloxy, n-hex-3-yn-1-ylcarbonyloxy,n-hex-3-yn-2-ylcarbonyloxy, 3-methylpent-1-yn-1-ylcarbonyloxy,3-methylpent-1-yn-3-ylcarbonyloxy, 3-methylpent-1-yn-4-ylcarbonyloxy,3-methylpent-1-yn-5-ylcarbonyloxy, 4-methylpent-1-yn-1-ylcarbonyloxy,4-methylpent-2-yn-4-ylcarbonyloxy, or 4-methylpent-2-yn-5-ylcarbonyloxy,in particular prop-2-yn-1-ylcarbonyloxy;

(C₂ -C₆ -alkynyl)carbonyloxy: ethynylcarbonyloxy or one of the radicalsmentioned under (C₃ -C₆ -alkynyl)carbonyloxy, in particularethynylcarbonyloxy or prop-2-yn-1-ylcarbonyloxy;

C₃ -C₆ -alkynylsulfonyloxy: prop-1-yn-1-ylsulfonyloxy,prop-2-yn-1-ylsulfonyloxy, n-but-1-yn-1-ylsulfonyloxy,n-but-1-yn-3-ylsulfonyloxy, n-but-1-yn-4-ylsulfonyloxy,n-but-2-yn-1-ylsulfonyloxy, n-pent-1-yn-1-ylsulfonyloxy,n-pent-1-yn-3-ylsulfonyloxy, n-pent-1-yn-4-ylsulfonyloxy,n-pent-1-yn-5-ylsulfonyloxy, n-pent-2-yn-1-ylsulfonyloxy,n-pent-2-yn-4-ylsulfonyloxy, n-pent-2-yn-5-ylsulfonyloxy,3-methylbut-1-yn-3-ylsulfonyloxy, 3-methylbut-1-yn-4-ylsulfonyloxy,n-hex-1-yn-1-ylsulfonyloxy, n-hex-1-yn-3-ylsulfonyloxy,n-hex-1-yn-4-ylsulfonyloxy, n-hex-1-yn-5-ylsulfonyloxy,n-hex-1-yn-6-ylsulfonyloxy, n-hex-2-yn-1-ylsulfonyloxy,n-hex-2-yn-4-ylsulfonyloxy, n-hex-2-yn-5-ylsulfonyloxy,n-hex-2-yn-6-ylsulfonyloxy, n-hex-3-yn-1-ylsulfonyloxy,n-hex-3-yn-2-ylsulfonyloxy, 3-methylpent-1-yn-1-ylsulfonyloxy,3-methylpent-1-yn-3-ylsulfonyloxy, 3-methylpent-1-yn-4-ylsulfonyloxy,3-methylpent-1-yn-5-ylsulfonyloxy, 4-methylpent-1-yn-1-ylsulfonyloxy,4-methylpent-2-yn-4-ylsulfonyloxy or 4-methylpent-2-yn-5-ylsulfonyloxy,in particular prop-2-yn-1-ylsulfonyloxy;

(C₃ -C₆ -alkynyl)carbonylthio: prop-1-yn-1-ylcarbonylthio,prop-2-yn-1-ylcarbonylthio, n-but-1-yn-1-ylcarbonylthio,n-but-1-yn-3-ylcarbonylthio, n-but-1-yn-4-ylcarbonylthio,n-but-2-yn-1-ylcarbonylthio, n-pent-1-yn-1-ylcarbonylthio,n-pent-1-yn-3-ylcarbonylthio, n-pent-1-yn-4-ylcarbonylthio,n-pent-1-yn-5-ylcarbonylthio, n-pent-2-yn-1-ylcarbonylthio,n-pent-2-yn-4-ylcarbonylthio, n-pent-2-yn-5-ylcarbonylthio,3-methylbut-1-yn-3-ylcarbonylthio, 3-methylbut-1-yn-4-ylcarbonylthio,n-hex-1-yn-1-ylcarbonylthio, n-hex-1-yn-3-ylcarbonylthio,n-hex-1-yn-4-ylcarbonylthio, n-hex-1-yn-5-ylcarbonylthio,n-hex-1-yn-6-ylcarbonylthio, n-hex-2-yn-1-ylcarbonylthio,n-hex-2-yn-4-ylcarbonylthio, n-hex-2-yn-5-ylcarbonylthio,n-hex-2-yn-6-ylcarbonylthio, n-hex-3-yn-1-ylcarbonylthio,n-hex-3-yn-2-ylcarbonylthio, 3-methylpent-1-yn-1-ylcarbonylthio,3-methylpent-1-yn-3-ylcarbonylthio, 3-methylpent-1-yn-4-ylcarbonylthio,3-methylpent-1-yn-5-ylcarbonylthio, 4-methylpent-1-yn-1-ylcarbonylthio,4-methylpent-2-yn-4-ylcarbonylthio or4-methylpent-2-yn-5-ylcarbonylthio, in particularprop-2-yn-1-ylcarbonylthio;

(C₂ -C₆ -alkynyl)carbonylthio: ethynylcarbonylthio or one of theradicals mentioned under (C₃ -C₆ -alkynyl)carbonylthio, in particularethynylcarbonylthio or prop-2-yn-1-ylcarbonylthio;

(C₁ -C₆ -alkoxy)carbonyl-C₂ -C₆ -alkenyl: C₂ -C₆ -alkenyl which issubstituted by (C₁ -C₆ -alkoxy)carbonyl as mentioned above, ie. forexample methoxycarbonylprop-2-en-1-yl;

C₃ -C₆ -alkenyloxy-C₁ -C₆ -alkyl: C₁ -C₆ -alkyl which is substituted byC₃ -C₆ -alkenyloxy as mentioned above, preferably by allyloxy,2-methylprop-2-en-1-yloxy, but-1-en-3-yloxy, but-1-en-4-yloxy orbut-2-en-1-yloxy, ie. for example allyloxymethyl, 2-allyloxyethyl orbut-1-en-4-yloxymethyl;

C₃ -C₆ -alkynyloxy-C₁ -C₆ -alkyl: C₁ -C₆ -alkyl which is substituted byC₃ -C₆ -alkynyloxy as mentioned above, preferably by propargyloxy,but-1-yn-3-yloxy, but-1-yn-4-yloxy or but-2-yn-1-yloxy, ie. for examplepropargyloxymethyl or 2-propargyloxyethyl;

C₃ -C₇ -cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl orcycloheptyl, in particular cyclopentyl or cyclohexyl;

C₃ -C₆ -cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;

C₃ -C₈ -cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cycloheptyl or cyclooctyl, in particular cyclopentyl or cyclohexyl;

C₃ -C₈ -cycloalkyl-C₁ -C₄ -alkyl: cyclopropylmethyl, cyclobutylmethyl,cyclopentylmethyl, cyclohexylmethyl, cycloheptylmethyl,cyclooctylmethyl, 1-(cyclopropyl)ethyl, 1-(cyclobutyl)ethyl,1-(cyclopentyl)ethyl, 1-(cyclohexyl)ethyl, 1-(cycloheptyl)ethyl,1-(cyclooctyl)ethyl, 2-(cyclopropyl)ethyl, 2-(cyclobutyl)ethyl,2-(cyclopentyl)ethyl, 2-(cyclohexyl)ethyl, 2-(cycloheptyl)ethyl,2-(cyclooctyl)ethyl, 3-(cyclopropyl)propyl, 3-(cyclobutyl)propyl,3-(cyclopentyl)propyl, 3-(cyclohexyl)propyl, 3-(cycloheptyl)propyl,3-(cyclooctyl)propyl, 4-(cyclopropyl)butyl, 4-(cyclobutyl)butyl,4-(cyclopentyl)butyl, 4-(cyclohexyl)butyl, 4-(cycloheptyl)butyl or4-(cyclooctyl)butyl, in particular cyclopentylmethyl orcyclohexylmethyl;

C₃ -C₆ -cycloalkyloxy: cyclopropyloxy, cyclobutyloxy, cyclopentyloxy orcyclohexyloxy;

C₃ -C₆ -cycloalkylthio: cyclopropylthio, cyclobutylthio, cyclopentylthioor cyclohexylthio;

C₃ -C₆ -cycloalkylcarbonyloxy: cyclopropylcarbonyloxy,cyclobutylcarbonyloxy, cyclopentylcarbonyloxy or cyclohexylcarbonyloxy;

C₃ -C₆ -cycloalkylsulfonyloxy: cyclopropylsulfonyloxy,cyclobutylsulfonyloxy, cyclopentylsulfonyloxy or cyclohexylsulfonyloxy;

C₃ -C₆ -cycloalkyloxy-C₁ -C₄ -alkyl: cyclopropyloxymethyl,cyclobutyloxymethyl, cyclopentyloxymethyl, cyclohexyloxymethyl,1-cyclopropyloxy)ethyl, 1-(cyclobutyloxy)ethyl, 1-(cyclopentyloxy)ethyl,1-(cyclohexyloxy)ethyl, 2-(cyclopropyloxy)ethyl, 2-(cyclobutyloxy)ethyl,2-(cyclopentyloxy)ethyl, 2-(cyclohexyloxy)ethyl, 3-(cyclopropyloxy)propyl, 3-(cyclobutyloxy)propyl, 3-(cyclopentyloxy)propyl,3-(cyclohexyloxy)propyl, 4-(cyclopropyloxy)butyl,4-(cyclobutyloxy)butyl, 4-(cyclopentyloxy)butyl or4-(cyclohexyloxy)butyl, in particular cyclopentyloxymethyl,cyclohexyloxymethyl or 2-(cyclopentyloxy)ethyl;

C₅ -C₇ -cycloalkenyloxy: cyclopent-1-enyloxy, cyclopent-2-enyloxy,cyclopent-3-enyloxy, cyclohex-1-enyloxy, cyclohex-2-enyloxy,cyclohex-3-enyloxy, cyclohept-1-enyloxy, cyclohept-2-enyloxy,cyclohept-3-enyloxy or cyclohept-4-enyloxy;

C₁ -C₃ -alkylene: methylene, 1,2-ethylene or 1,3-propylene.

3 - to 7-membered heterocyclyl--which may be attached directly or via anoxygen, alkoxy, alkenyloxy or alkynyloxy bridge--is a saturated,partially or fully unsaturated or aromatic heterocycle having one tothree hetero atoms selected from a group consisting of

one to three nitrogen atoms,

one or two oxygen atoms and

one or two sulfur atoms.

Examples of saturated heterocycles which may contain a carbonyl orthiocarbonyl ring member are:

oxiranyl, thiiranyl, aziridin-1-yl, aziridin-2-yl, diaziridin-1-yl,diaziridin-3-yl, oxetan-2-yl, oxetan-3-yl, thietan-2-yl, thietan-3-yl,azetidin-1-yl, azetidin-2-yl, azetidin-3-yl, tetrahydrofuran-2-yl,tetrahydrofuran-3-yl, tetrahydrothiophen-2-yl, tetrahydrothiophen-3-yl,pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, 1,3-dioxolan-2-yl,1,3-dioxolan-4-yl, 1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl,1,3-oxathiolan-5-yl, 1,3-oxazolidin-2-yl, 1,3-oxazolidin-3-yl,1,3-oxazolidin-4-yl, 1,3-oxazolidin-5-yl, 1,2-oxazolidin-2-yl,1,2-oxazolidin-3-yl, 1,2-oxazolidin-4-yl, 1,2-oxazolidin-5-yl,1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl, pyrrolidin-1-yl,pyrrolidin-2-yl, pyrrolidin-5-yl, tetrahydropyrazol-1-yl,tetrahydropyrazol-3-yl, tetrahydropyrazol-4-yl, tetrahydropyran-2-yl,tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-2-yl,tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, piperidin-1-yl,piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, 1,3-dioxan-2-yl,1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 1,3-oxathian-2-yl,1,3-oxathian-4-yl, 1,3-oxathian-5-yl, 1,3-oxathian-6-yl,1,4-oxathian-2-yl, 1,4-oxathian-3-yl, morpholin-2-yl, morpholin-3-yl,morpholin-4-yl, hexahydropyridazin-1-yl, hexahydropyridazin-3-yl,hexahydropyridazin-4-yl, hexahydropyrimidin-1-yl,hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl,hexahydropyrimidin-5-yl, piperazin-1-yl, piperazin-2-yl, piperazin-3-yl,hexahydro-1,3,5-triazin-1-yl, hexahydro-1,3,5-triazin-2-yl, oxepan-2-yl,oxepan-3-yl, oxepan-4-yl, thiepan-2-yl, thiepan-3-yl, thiepan-4-yl,1,3-dioxepan-2-yl, 1,3-dioxepan-4-yl, 1,3-dioxepan-5-yl,1,3-dioxepan-6-yl, 1,3-dithiepan-2-y, 1,3-dithiepan-2-yl,1,3-dithiepan-2-yl, 1,3-dithiepan-2-yl, 1,4-dioxepan-2-yl,1,4-dioxepan-7-yl, hexahydroazepin-1-yl, hexahydroazepin-2-yl,hexahydroazepin-3-yl, hexahydroazepin-4-yl, hexahydro-1,3-diazepin-1-yl, hexahydro-1,3-diazepin-2-yl, hexahydro-1,3-diazepin-4-yl,hexahydro-1,4-diazepin-1-yl and hexahydro-1,4-diazepin-2-yl;

Examples of unsaturated heterocycles which may contain a carbonyl orthiocarbonyl ring member are: dihydrofuran-2-yl, 1,2-oxazolin-3-yl,1,2-oxazolin-5-yl, 1,3-oxazolin-2-yl.

Preferred heteroaromatics are the 5- and 6-membered heteroaromatics, ie.for example:

furyl, such as 2-furyl and 3-furyl, thienyl, such as 2-thienyl and3-thienyl, pyrrolyl, such as 2-pyrrolyl and 3-pyrrolyl, isoxazolyl, suchas 3-isoxazolyl, 4-isoxazolyl and 5-isoxazolyl, isothiazolyl, such as3-isothiazolyl, 4-isothiazolyl and 5-isothiazolyl, pyrazolyl, such as3-pyrazolyl, 4-pyrazolyl and 5-pyrazolyl, oxazolyl, such as 2-oxazolyl,4-oxazolyl and 5-oxazolyl, thiazolyl, such as 2-thiazolyl, 4-thiazolyland 5-thiazolyl, imidazolyl, such as 2-imidazolyl and 4-imidazolyl,oxadiazolyl, such as 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and1,3,4-oxadiazol-2-yl, thiadiazolyl, such as 1,2,4-thiadiazol-3-yl,1,2,4-thiadiazol-5-yl and 1,3,4-thiadiazol-2-yl, triazolyl, such as1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl and 1,2,4-triazol-4-yl,pyridinyl, such as 2-pyridinyl, 3-pyridinyl and 4-pyridinyl,pyridazinyl, such as 3-pyridazinyl and 4-pyridazinyl, pyrimidinyl, suchas 2-pyrimidinyl, 4-pyrimidinyl and 5-pyrimidinyl, and furthermore2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl, in particularpyridyl, pyrimidyl, furanyl and thienyl.

All phenyl and heterocyclic rings are preferably unsubstituted or carryone substituent.

With a view to the use of the compounds of the formula I according tothe invention as herbicides, the variables preferably have the followingmeanings, in each case either on their own or in combination:

X is oxygen;

R¹ is cyano, C₁ -C₄ -haloalkyl or C₁ -C₄ -alkylsulfonyl, in particularC₁ -C₄ -haloalkyl, particularly preferably trifluoromethyl;

R³ is hydrogen;

R⁴ is cyano or halogen, in particular halogen, particularly preferablychlorine;

R⁵ is hydrogen or halogen, in particular hydrogen, fluorine or chlorine,particularly preferably fluorine;

R⁶ is hydrogen;

R⁷ is cyano or halogen, in particular cyano or chlorine, particularlypreferably chlorine;

R⁸ is

1) hydrogen, hydroxyl, mercapto, cyano, nitro, halogen, C₁ -C₆ -alkyl,C₁ -C₆ -haloalkyl, C₁ -C₆ -haloalkoxy, C₁ -C₆ -haloalkylthio, C₁ -C₆-alkylthio-(C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆ -alkyl)iminooxycarbonyl, C₁-C₆ -alkoxy-C₁ -C₆ -alkyl, C₁ -C₆ -alkoxyamino-C₁ -C₆ -alkyl, C₁ -C₆-alkoxy-C₁ -C₆ -alkylamino-C₁ -C₆ -alkyl,

2) C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, C₃ -C₆ -cycloalkoxy, C₃ -C₆-cycloalkylthio, C₂ -C₆ -alkenyloxy, C₂ -C₆ -alkenylthio, C₂ -C₆-alkynyloxy, C₂ -C₆ -alkynylthio, (C₁ -C₆ -alkyl)carbonyloxy, (C₁ -C₆-alkyl)carbonylthio, (C₁ -C₆ -alkoxy)carboxyloxy, (C₂ -C₆-alkenyl)carbonyloxy, (C₂ -C₆ -alkenyl)carbonylthio, (C₂ -C₆-alkynyl)carbonyloxy, (C₂ -C₆ -alkynyl)carbonylthio, C₁ -C₆-alkylsulfonyloxy or C₁ -C₆ -alkylsulfonyl, where each of the 17last-mentioned radicals may, if desired, carry one to threesubstituents, in each case selected from the group consisting of

halogen, nitro, cyano, hydroxyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -alkoxy, C₃-C₆ -cycloalkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆ -alkynyloxy, C₁ -C₆-alkoxy-C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylsulfinyl, C₁ -C₆-alkylsulfonyl, C₁ -C₆ -alkylideneaminooxy, oxo, ═N--OR¹⁸,

the phenyl, phenoxy or phenylsulfonyl group, which may be unsubstitutedor may carry one to three substituents, in each case selected from thegroup consisting of halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆-haloalkyl, C₁ -C₆ -alkoxy and (C₁ -C₆ -alkoxy)carbonyl,

a group --CO--R¹⁹, --CO--OR¹⁹, --CO--SR¹⁹, --CO--N(R¹⁹)R²⁰, --OCO--R¹⁹,--OCO--OR¹⁹, --OCO--SR¹⁹, --OCO--N(R¹⁹)R²⁰ or --N(R¹⁹)--R²⁰,

the group --C(R²¹)═N--OR¹⁸ ;

3) --CO--R²², --CS--R²², --C(NR²³)--R²², --C(R²²)(Z¹ R²⁴)(Z² R²⁵), whereZ¹ and Z² are each oxygen or sulfur, --C(R²²)═C(R²⁶)--CN,--C(R²²)═C(R²⁶)--CO--R²⁷, --CH(R²²)--CH(R²⁶)--CO--R²⁷,--C(R²²)═C(R²⁶)--CH₂ --CO--R²⁷, --C(R²²)═C(R²⁶)--C(R²⁸)═C(R²⁹)--CO--R²⁷,--C(R²²)═C(R²⁶)--CH₂ --CH(R³⁰)--CO--R²⁷, --CO--OR³¹, --CO--SR³¹,--CO--N(R³¹)--OR¹⁸, --C.tbd.C--CO--NH--OR¹⁸,--C.tbd.C--CO--N(R³¹)--OR¹⁸, --C.tbd.C--CS--NH--OR¹⁸,--C.tbd.C--CS--N(R³¹)--OR¹⁸, --C(R²²)═C(R²⁶)--CO--NH--OR¹⁸,--C(R²²)═C(R²⁶)--CO--N(R³¹)--OR¹⁸, --C(R²²)═C(R²⁶)--CS--NH--OR¹⁸,--C(R²²)═C(R²⁶)--CS--N(R³¹)--OR¹⁸, --C(R²²)═C(R²⁶)--C(R²¹)═N--OR¹⁸,--C(R²¹)═N--OR¹⁸, --C.tbd.C--C(R²¹)═N--OR¹⁸, --C(Z¹ R²⁴)(Z² R²⁵)--OR³¹,--C(Z¹ R²⁴)(Z² R²⁵)--SR³¹, --C(Z¹ R²⁴)(Z² R²⁵)--N(R³²)R³³, --N(R³²)R³³or --CON(R³²)R³³ ;

R⁸ is in particular --CO--R²², --CS--R²², --C(NR²³)--R²², --C(R²²)(Z¹R²⁴)(Z² R²⁵), where Z¹ and Z² are each oxygen or sulfur,--C(R²²)═C(R²⁶)--CN, --C(R²²)═C(R²⁶)--CO--R²⁷,--CH(R²²)--CH(R²⁶)--CO--R²⁷, --C(R²²)═C(R²⁶)--CH₂ --CO--R²⁷,--C(R²²)═C(R²⁶)--C(R²⁸)═C(R²⁹)--CO--R²⁷, --C(R²²)═C(R²⁶)--CH₂--CH(R³⁰)--CO--R²⁷, --CO--OR³¹, --CO--SR³¹, --CO--N(R³¹)--OR¹⁸,--C.tbd.C--CO--NH--OR¹⁸, --C.tbd.C--CO--N(R³¹)--OR¹⁸,--C.tbd.C--CS--NH--OR¹⁸, --C.tbd.C--CS--N(R³¹)--OR¹⁸,--C(R²²)═C(R²⁶)--CO--NH--OR¹⁸, --C(R²²)═C(R²⁶)--CO--N(R³¹)--OR¹⁸,--C(R²²)═C(R²⁶)--CS--NH--OR¹⁸, --C(R²²)═C(R²⁶)--CS--N(R³¹)--OR¹⁸,--C(R²²)═C(R²⁶)--C(R²¹)═N--OR¹⁸, --C(R²¹)═N--OR¹⁸,--C.tbd.C--C(R²¹)═N--OR¹⁸, --C(Z¹ R²⁴)(Z² R²⁵)--OR³¹, --C(Z¹ R²⁴)(Z²R²⁵)--SR³¹, --C(Z¹ R²⁴)(Z² R²⁵)--N(R³²)R³³, --N(R³²)R³³ or --CON(R³²)R³³; particularly preferably --CO--R²², --C(NR²³)--R²² oder--C(R²²)═C(R²⁶)--CO--R²⁷ ;

R¹⁸ is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -cycloalkyl,C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, hydroxy-C₁ -C₆ -alkyl, C₁ -C₆-alkoxy-C₁ -C₆ -alkyl, C₁ -C₆ -alkylthio-C₁ -C₆ -alkyl, cyano-C₁ -C₆-alkyl, (C₁ -C₆ -alkyl)carbonyl-C₁ -C₆ -alkyl, (C₁ -C₆-alkoxy)carbonyl-C₁ -C₆ -alkyl, (C₁ -C₆ -alkoxy)carbonyl-C₂ -C₆-alkenyl, (C₁ -C₆ -alkyl)carbonyloxy-C₁ -C₆ -alkyl or phenyl-C₁ -C₆-alkyl, where the phenyl ring may, if desired, carry one to threesubstituents, in each case selected from the group consisting of cyano,nitro, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy and (C₁-C₆ -alkoxy)carbonyl;

R¹⁹ is hydrogen, C₁ -C₆ -alkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -alkenyl, C₃-C₆ -alkynyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, (C₁ -C₆ -alkoxy)carbonyl-C₁-C₆ -alkyl, (C₃ -C₆ -alkenyloxy)carbonyl-C₁ -C₆ -alkyl, phenyl orphenyl-C₁ -C₆ -alkyl, where the phenyl group and the phenyl ring of thephenylalkyl group may be unsubstituted or may carry one to threeradicals, in each case selected from the group consisting of halogen,nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy and (C₁-C₆ -alkyl)carbonyl;

R²⁰ is hydrogen, hydroxyl, C₁ -C₆ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₆-alkoxy, (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkoxy, C₃ -C₆ -alkenyl or C₃-C₆ -alkenyloxy;

R²¹ is

hydrogen, halogen,

C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₃-C₆ -alkenyloxy, C₁ -C₆ -alkylthio, C₁ -C₆ -haloalkylthio, (C₁ -C₆-alkyl)carbonyloxy, (C₁ -C₆ -haloalkyl)carbonyloxy, C₁ -C₆-alkylsulfonyloxy or C₁ -C₆ -haloalkylsulfonyloxy, where the 11last-mentioned radicals may carry one of the following substituents:hydroxyl, cyano, hydroxycarbonyl, C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, (C₁-C₆ -alkyl)carbonyl, (C₁ -C₆ -alkoxy)carbonyl, (C₁ -C₆-alkyl)aminocarbonyl, di(C₁ -C₆ -alkyl)aminocarbonyl, (C₁ -C₆-alkyl)carbonyloxy, C₁ -C₆ -alkoxy-(C₁ -C₆ -alkyl)aminocarbonyl;

a 3- to 7-membered azaheterocycle which is attached to the nitrogen atomvia a carbonyl bridge and which may, in addition to carbon ring members,also contain one oxygen or sulfur atom as ring member;

(C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆ -haloalkyl)carbonyl, (C₁ -C₆-alkoxy)carbonyl, (C₁ -C₆ -alkoxy)carbonyloxy, (C₁ -C₆-alkyl)carbonylthio, (C₁ -C₆ -haloalkyl)carbonylthio, (C₁ -C₆-alkoxy)carbonylthio, C₂ -C₆ -alkenyl, C₂ -C₆ -alkenylthio, C₃ -C₆-alkynyl, C₃ -C₆ -alkynyloxy, C₃ -C₆ -alkynylthio, (C₂ -C₆-alkynyl)carbonyloxy, C₃ -C₆ -alkynylsulfonyloxy, C₃ -C₆ -cycloalkyl, C₃-C₆ -cycloalkyloxy, C₃ -C₆ -cycloalkylthio, (C₃ -C₆-cycloalkyl)carbonyloxy, C₃ -C₆ -cycloalkylsulfonyloxy;

phenyl, phenoxy, phenylthio, benzoyloxy, phenylsulfonyloxy, phenyl-C₁-C₆ -alkyl, phenyl-C₁ -C₆ -alkoxy, phenyl-C₁ -C₆ -alkylthio, phenyl-(C₁-C₆ -alkyl)carbonyloxy or phenyl-(C₁ -C₆ -alkyl)sulfonyloxy, where thephenyl rings of the 10 last-mentioned radicals may be unsubstituted ormay themselves carry one to three substituents, in each case selectedfrom the group consisting of cyano, nitro, halogen, C₁ -C₆ -alkyl, C₁-C₆ -haloalkyl, C₁ -C₆ -alkoxy and (C₁ -C₆ -alkoxy)carbonyl;

R²² is hydrogen, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₂ -C₆-alkenyl, C₂ -C₆ -alkynyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -alkoxy-C₁ -C₆-alkyl or (C₁ -C₆ -alkoxy)carbonyl;

R²³ is hydrogen, hydroxyl, C₁ -C₆ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆-alkynyl, C₃ -C₇ -cycloalkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy-C₁ -C₆-alkyl, C₁ -C₆ -alkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆ -alkynyloxy, C₃ -C₆-cycloalkoxy, C₅ -C₇ -cycloalkenyloxy, C₁ -C₆ -haloalkoxy, C₃ -C₆-haloalkenyloxy, hydroxy-C₁ -C₆ -alkoxy, cyano-C₁ -C₆ -alkoxy, C₃ -C₆-cycloalkyl-C₁ -C₆ -alkoxy, C₁ -C₆ -alkoxy-C₁ -C₆ -alkoxy, C₁ -C₆-alkoxy-C₃ -C₆ -alkenyloxy, (C₁ -C₆ -alkyl)carbonyloxy, (C₁ -C₆-haloalkyl)carbonyloxy, (C₁ -C₆ -alkyl)carbamoyloxy, (C₁ -C₆-haloalkyl)carbamoyloxy, (C₁ -C₆ -alkyl)carbonyl-C₁ -C₆ -alkyl, (C₁ -C₆-alkyl)carbonyl-C₁ -C₆ -alkoxy, (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkyl,(C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio-C₁ -C₆-alkoxy, di(C₁ -C₆ -alkyl)amino-C₁ -C₆ -alkoxy, phenyl which may itselfcarry one to three substituents, in each case selected from the groupconsisting of cyano, nitro, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl,C₂ -C₆ -alkenyl, C₁ -C₆ -alkoxy and (C₁ -C₆ -alkoxy)carbonyl, phenyl-C₁-C₆ -alkoxy, phenyl-C₃ -C₆ -alkenyloxy or phenyl-C₃ -C₆ -alkynyloxy,where in each case one or two methylene groups of the hydrocarbon chainsmay be replaced by --O--, --S-- or --N(C₁ -C₆ -alkyl)-, and where eachphenyl ring may be unsubstituted or may itself carry one to threesubstituents, in each case selected from the group consisting of cyano,nitro, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₂ -C₆ -alkenyl, C₁-C₆ -alkoxy and (C₁ -C₆ -alkoxy)carbonyl, heterocyclyl, heterocyclyl-C₁-C₆ -alkoxy, heterocyclyl-C₃ -C₆ -alkenyloxy or heterocyclyl-C₃ -C₆-alkynyloxy, where in each case one or two methylene groups of thehydrocarbon chains may be replaced by --O--, --S-- or --N(C₁ -C₆-alkyl)-, and where each heterocycle may be 3- to 7-membered, saturated,unsaturated or aromatic and contains one to four hetero atoms selectedfrom the group consisting of two oxygen atoms, two sulfur atoms and 4nitrogen atoms, and is either unsubstituted or itself carries one tothree substituents, in each case selected from the group consisting ofcyano, nitro, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₂ -C₆-alkenyl, C₁ -C₆ -alkoxy and (C₁ -C₆ -alkoxy)carbonyl, or --N(R³⁵)R³⁶where R³⁵ and R³⁶ are each hydrogen, C₁ -C₆ -alkyl, C₃ -C₆ -alkenyl, C₃-C₆ -alkynyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy-C₁-C₆ -alkyl, (C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆ -alkoxy)carbonyl, (C₁ -C₆-alkoxy)carbonyl-C₁ -C₆ -alkyl, (C₁ -C₆ -alkoxy)carbonyl-C₂ -C₆ -alkenylwhere the alkenyl chain may additionally carry one to three halogenand/or cyano radicals, or are phenyl which may be unsubstituted or mayitself carry one to three substituents, in each case selected from thegroup consisting of cyano, nitro, halogen, C₁ -C₆ -alkyl, C₁ -C₆-haloalkyl, C₃ -C₆ -alkenyl, C₁ -C₆ -alkoxy and (C₁ -C₆-alkoxy)carbonyl, or where R³⁵ and R³⁶ together with the linkingnitrogen atom form a saturated or unsaturated 4- to 7-memberedazaheterocycle which, in addition to carbon ring members, may, ifdesired, also contain one of the following members: --O--, --S--, --N═,--NH-- or --N(C₁ -C₆ -alkyl)-;

R²⁴ and R²⁵ independently of one another are each C₁ -C₆ -alkyl, C₁ -C₆-haloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₁ -C₆ -alkoxy-C₁ -C₆-alkyl or together are a saturated or unsaturated 2- to 4-memberedhydrocarbon chain which may carry an oxo substituent, where one memberof this chain may be replaced by a bridge --O--, --S--, --N═, --NH-- or--N(C₁ -C₆ -alkyl)- which is not adjacent to the variables Z¹ and Z²,and where the hydrocarbon chain may carry one to three radicals, in eachcase selected from the group consisting of cyano, nitro, amino, halogen,C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl, C₁ -C₆ -alkoxy, C₂ -C₆ -alkenyloxy, C₂-C₆ -alkynyloxy, C₁ -C₆ -haloalkyl, cyano-C₁ -C₆ -alkyl, hydroxy-C₁ -C₆-alkyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, C₃ -C₆ -alkenyloxy-C₁ -C₆ -alkyl,C₃ -C₆ -alkynyloxy-C₁ -C₆ -alkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆-cycloalkoxy, carboxyl, (C₁ -C₆ -alkoxy)carbonyl, (C₁ -C₆-alkyl)carbonyloxy-C₁ -C₆ -alkyl and phenyl which may itself beunsubstituted or may carry one to three substituents, in each caseselected from the group consisting of cyano, nitro, amino, halogen, C₁-C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy and (C₁ -C₆-alkoxy)carbonyl, and where the hydrocarbon chain may also besubstituted by a fused-on or spiro-linked 3- to 7-membered ring whichmay contain as ring members one or two hetero atoms selected from thegroup consisting of oxygen, sulfur, nitrogen and C₁ -C₆-alkyl-substituted nitrogen, and which may, if desired, itself carry oneor two of the following substituents: cyano, C₁ -C₆ -alkyl, C₂ -C₆-alkenyl, C₁ -C₆ -alkoxy, cyano-C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl and (C₁-C₆ -alkoxy)carbonyl;

R²⁶ is hydrogen, cyano, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁-C₆ -alkoxy, (C₁ -C₆ -alkyl)carbonyl or (C₁ -C₆ -alkoxy)carbonyl;

R²⁷ is hydrogen, O--R³⁴, S--R³⁴, C₁ -C₆ -alkyl which may carry one ortwo C₁ -C₆ -alkoxy substituents, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, C₁-C₆ -haloalkyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -alkylthio-C₁ -C₆ -alkyl, C₁-C₆ -alkyliminooxy, --N(R³²)R³³ or phenyl which may be unsubstituted ormay carry one to three substituents, in each case selected from thegroup consisting of cyano, nitro, halogen, C₁ -C₆ -alkyl, C₂ -C₆-alkenyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy and (C₁ -C₆-alkoxy)carbonyl;

R²⁸ is hydrogen, cyano, halogen, C₁ -C₆ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆-alkynyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, (C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆-alkoxy)carbonyl, --N(R³²)R³³ or phenyl which may itself carry one tothree substituents, in each case selected from the group consisting ofcyano, nitro, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₆-alkenyl, C₁ -C₆ -alkoxy and (C₁ -C₆ -alkoxy)carbonyl;

R²⁹ is hydrogen, cyano, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆-haloalkyl, (C₁ -C₆ -alkyl)carbonyl or (C₁ -C₆ -alkoxy)carbonyl;

R³⁰ is hydrogen, cyano, C₁ -C₆ -alkyl or (C₁ -C₆ -alkoxy)carbonyl;

R³¹ and R³⁴ independently of one another are each hydrogen, C₁ -C₆-alkyl, C₁ -C₆ -haloalkyl, C₂ -C₆ -alkenyl or C₂ -C₆ -alkynyl, where the4 last-mentioned groups may in each case carry one or two of thefollowing radicals: cyano, halogen, hydroxyl, hydroxycarbonyl, C₁ -C₆-alkoxy, C₁ -C₆ -alkylthio, (C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆-alkoxy)carbonyl, (C₁ -C₆ -alkyl)carbonyloxy, (C₃ -C₆-alkenyloxy)carbonyl or a 3- to 7-membered azaheterocycle which isattached to the nitrogen atom via a carbonyl bridge and which may, inaddition to carbon ring members, also contain one oxygen or sulfur atomas ring member; or are (C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆-haloalkyl)carbonyl, (C₁ -C₆ -alkoxy)carbonyl, C₁ -C₆-alkylaminocarbonyl, di(C₁ -C₆ -alkyl)aminocarbonyl, C₁ -C₆-alkyloximino-C₁ -C₆ -alkyl, C₃ -C₆ -cycloalkyl, phenyl or phenyl-C₁ -C₆-alkyl, where the phenyl rings may be unsubstituted or may themselvescarry one to three substituents, in each case selected from the groupconsisting of cyano, nitro, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl,C₁ -C₆ -alkoxy and (C₁ -C₆ -alkoxy)carbonyl;

R³² and R³³ independently of one another are each hydrogen, C₁ -C₆-alkyl, C₃ -C₆ -alkenyl, C₂ -C₆ -alkynyl, C₃ -C₆ -cycloalkyl, C₁ -C₆-haloalkyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, (C₁ -C₆ -alkyl)carbonyl, (C₁-C₆ -alkoxy)carbonyl, (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkyl, (C₁ -C₆-alkoxy)carbonyl-C₂ -C₆ -alkenyl, where the alkenyl chain mayadditionally carry one to three halogen and/or cyano radicals, or are C₁-C₆ -alkylsulfonyl, (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkylsulfonyl,phenyl or phenylsulfonyl, where the two phenyl rings may beunsubstituted or may themselves carry one to three substituents, in eachcase selected from the group consisting of cyano, nitro, halogen, C₁ -C₆-alkyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -alkenyl, C₁ -C₆ -alkoxy and (C₁ -C₆-alkoxy)carbonyl,

or R³² and R³³ together with the linking nitrogen atom are a saturatedor unsaturated 4- to 7-membered azaheterocycle which, in addition tocarbon ring members, may, if desired, contain one of the followingmembers: --O--, --S--, --N═, --NH-- or --N(C₁ -C₆ -alkyl)-.

Very generally, preference is also given to those compounds I where R⁷is in position α and R⁸ is in position β.

Very particular preference is given to the substituted3-phenylisoxazolines of the formula Ia (= I where X=oxygen; R¹=trifluoromethyl; R², R³, R⁶ =hydrogen; R⁴ =chlorine; R⁵ =fluorine; R⁷is in position α; R⁸ is in position β), in particular the compounds Ia.1to Ia.160 listed in Table 1 below:

                  TABLE 1                                                         ______________________________________                                                                       Ia                                              ##STR3##                                                                     No.   R.sup.7                                                                              R.sup.8                                                          ______________________________________                                        Ia.1  CN     CO--OCH.sub.3                                                    Ia.2  Cl     CO--OCH.sub.3                                                    Ia.3  CN     CO--OC.sub.2 H.sub.5                                             Ia.4  Cl     CO--OC.sub.2 H.sub.5                                             Ia.5  CN     CO--OCH.sub.2 --CO--OCH.sub.3                                    Ia.6  Cl     CO--OCH.sub.2 --CO--OCH.sub.3                                    Ia.7  CN     CO--OCH.sub.2 --CO--OC.sub.2 H.sub.5                             Ia.8  Cl     CO--OCH.sub.2 --CO--OC.sub.2 H.sub.5                             Ia.9  CN     CO--OCH(CH.sub.3)--CO--OCH.sub.3                                 Ia.10 Cl     CO--OCH(CH.sub.3)--CO--OCH.sub.3                                 Ia.11 CN     CO--OCH(CH.sub.3)--CO--OC.sub.2 H.sub.5                          Ia.12 Cl     CO--OCH(CH.sub.3)--CO--OC.sub.2 H.sub.5                          Ia.13 CN     CO--OC(CH.sub.3).sub.2 --CO--OCH.sub.3                           Ia.14 Cl     CO--OC(CH.sub.3).sub.2 --CO--OCH.sub.3                           Ia.15 CN     CO--OC(CH.sub.3).sub.2 --CO--OC.sub.2 H.sub.5                    Ia.16 Cl     CO--OC(CH.sub.3).sub.2 --CO--OC.sub.2 H.sub.5                    Ia.17 CN     CO--OC(CH.sub.3).sub.2 --CO--OCH.sub.2 --CH═CH.sub.2         Ia.18 Cl     CO--OC(CH.sub.3).sub.2 --CO--OCH.sub.2 --CH═CH.sub.2         Ia.19 CN     CO--NH--OCH.sub.3                                                Ia.20 Cl     CO--NH--OCH.sub.3                                                Ia.21 CN     CO--NH--OCH.sub.2 --C.sub.6 H.sub.5                              Ia.22 Cl     CO--NH--OCH.sub.2 --C.sub.6 H.sub.5                              Ia.23 CN     C(N--OCH.sub.3)--OCH.sub.2 --CO--OCH.sub.3                       Ia.24 Cl     C(N--OCH.sub.3)--OCH.sub.2 --CO--OCH.sub.3                       Ia.25 CN     C(N--OCH.sub.3)--OCH.sub.2 --CO--OC.sub.2 H.sub.5                Ia.26 Cl     C(N--OCH.sub.3)--OCH.sub.2 --CO--OC.sub.2 H.sub.5                Ia.27 CN     C(N--OCH.sub.2 --C.sub.6 H.sub.5)--OCH.sub.2 --CO--OCH.sub.3     Ia.28 Cl     C(N--OCH.sub.2 --C.sub.6 H.sub.5)--OCH.sub.2 --CO--OCH.sub.3     Ia.29 CN     C(N--OCH.sub.2 --C.sub.6 H.sub.5)--OCH.sub.2 --CO--OC.sub.2                   H.sub.5                                                          Ia.30 Cl     C(N--OCH.sub.2 --C.sub.6 H.sub.5)--OCH.sub.2 --CO--OC.sub.2                   H.sub.5                                                          Ia.31 CN     C(N--OCH.sub.3)--OCH.sub.2 --CO--N(CH.sub.3).sub.2               Ia.32 Cl     C(N--OCH.sub.3)--OCH.sub.2 --CO--N(CH.sub.3).sub.2               Ia.33 CN     C(N--OCH.sub.2 --C.sub.6 H.sub.5)--OCH.sub.2 --CO--N(CH.sub.3                 ).sub.2                                                          Ia.34 Cl     C(N--OCH.sub.2 --C.sub.6 H.sub.5)--OCH.sub.2 --CO--N(CH.sub.3                 ).sub.2                                                          Ia.35 CN     C(N--OCH.sub.3)--OCH.sub.2 --CO--N(CH.sub.3)--OCH.sub.3          Ia.36 Cl     C(N--OCH.sub.3)--OCH.sub.2 --CO--N(CH.sub.3)--OCH.sub.3          Ia.37 CN     C(N--OCH.sub.2 --C.sub.6 H.sub.5)--OCH.sub.2 --CO--N(CH.sub.3                 )--OCH.sub.3                                                     Ia.38 Cl     C(N--OCH.sub.2 --C.sub.6 H.sub.5)--OCH.sub.2 --CO--N(CH.sub.3                 )--OCH.sub.3                                                     Ia.39 CN     C(N--OCH.sub.3)--OCH(CH.sub.3)--CO--OCH.sub.3                    Ia.40 Cl     C(N--OCH.sub.3)--OCH(CH.sub.3)--CO--OCH.sub.3                    Ia.41 CN     C(N--OCH.sub.3)--OCH(CH.sub.3)--CO--OC.sub.2 H.sub.5             Ia.42 Cl     C(N--OCH.sub.3)--OCH(CH.sub.3)--CO--OC.sub.2 H.sub.5             Ia.43 CN     C(N--OCH.sub.2 --C.sub.6 H.sub.5)--OCH(CH.sub.3)--CO--OCH.sub                 .3                                                               Ia.44 Cl     C(N--OCH.sub.2 --C.sub.6 H.sub.5)--OCH(CH.sub.3)--CO--OCH.sub                 .3                                                               Ia.45 CN     C(N--OCH.sub.2 --C.sub.6 H.sub.5)--OCH(CH.sub.3)--CO--OC.sub.                 2 H.sub.5                                                        Ia.46 Cl     C(N--OCH.sub.2 --C.sub.6 H.sub.5)--OCH(CH.sub.3)--CO--OC.sub.                 2 H.sub.5                                                        Ia.47 CN     C(N--OCH.sub.3)--OC(CH.sub.3).sub.2 --CO--OCH.sub.3              Ia.48 Cl     C(N--OCH.sub.3)--OC(CH.sub.3).sub.2 --CO--OCH.sub.3              Ia.49 CN     C(N--OCH.sub.3)--OC(CH.sub.3).sub.2 --CO--OC.sub.2 H.sub.5       Ia.50 Cl     C(N--OCH.sub.3)--OC(CH.sub.3).sub.2 --CO--OC.sub.2 H.sub.5       Ia.51 CN     C(N--OCH.sub.2 --C.sub.6 H.sub.5)--OC(CH.sub.3).sub.2                         --CO--OCH.sub.3                                                  Ia.52 Cl     C(N--OCH.sub.2 --C.sub.6 H.sub.5)--OC(CH.sub.3).sub.2                         --CO--OCH.sub.3                                                  Ia.53 CN     C(N--OCH.sub.2 --C.sub.6 H.sub.5)--OC(CH.sub.3).sub.2                         --CO--OC.sub.2 H.sub.5                                           Ia.54 Cl     C(N--OCH.sub.2 --C.sub.6 H.sub.5)--OC(CH.sub.3).sub.2                         --CO--OC.sub.2 H.sub.5                                           Ia.55 CN     CH═N--OCH.sub.3                                              Ia.56 Cl     CH═N--OCH.sub.3                                              Ia.57 CN     CH═N--OC.sub.2 H.sub.5                                       Ia.58 Cl     CH═N--OC.sub.2 H.sub.5                                       Ia.59 CN     CH═N--OCH.sub.2 --C.sub.6 H.sub.5                            Ia.60 Cl     CH═N--OCH.sub.2 --C.sub.6 H.sub.5                            Ia.61 CN     CH═N--OCH.sub.2 --CO--OCH.sub.3                              Ia.62 Cl     CH═N--OCH.sub.2 --CO--OCH.sub.3                              Ia.63 CN     CH═N--OCH(CH.sub.3)--CO--OCH.sub.3                           Ia.64 Cl     CH═N--OCH(CH.sub.3)--CO--OCH.sub.3                           Ia.65 CN     CH.sub.2 --N(CH.sub.3)--OCH.sub.3                                Ia.66 Cl     CH.sub.2 --N(CH.sub.3)--OCH.sub.3                                Ia.67 CN     CH.sub.2 --N(CH.sub.3)--OCH.sub.2 --C.sub.6 H.sub.5              Ia.68 Cl     CH.sub.2 --N(CH.sub.3)--OCH.sub.2 --C.sub.6 H.sub.5              Ia.69 CN     CH═C(Cl)--CO--OCH.sub.3                                      Ia.70 Cl     CH═C(Cl)--CO--OCH.sub.3                                      Ia.71 CN     CH═C(Cl)--CO--OC.sub.2 H.sub.5                               Ia.72 Cl     CH═C(Cl)--CO--OC.sub.2 H.sub.5                               Ia.73 CN     CH═C(Cl)--CO--OCH.sub.2 --CO--OCH.sub.3                      Ia.74 Cl     CH═C(Cl)--CO--OCH.sub.2 --CO--OCH.sub.3                      Ia.75 CN     CH═C(Cl)--CO--OCH.sub.2 --CO--OC.sub.2 H.sub.5               Ia.76 Cl     CH═C(Cl)--CO--OCH.sub.2 --CO--OC.sub.2 H.sub.5               Ia.77 CN     CH═C(Cl)--CO--OCH(CH.sub.3)--CO--OCH.sub.3                   Ia.78 Cl     CH═C(Cl)--CO--OCH(CH.sub.3)--CO--OCH.sub.3                   Ia.79 CN     CH═C(Cl)--CO--OCH(CH.sub.3)--CO--OC.sub.2 H.sub.5            Ia.80 Cl     CH═C(Cl)--CO--OCH(CH.sub.3)--CO--OC.sub.2 H.sub.5            Ia.81 CN     CH═C(Cl)--CO--N(CH.sub.3)--CH.sub.2 --CO--OCH.sub.3          Ia.82 Cl     CH═C(Cl)--CO--N(CH.sub.3)--CH.sub.2 --CO--OCH.sub.3          Ia.83 CN     CH═C(Cl)--CO--N(CH.sub.3)--CH.sub.2 --CO--OC.sub.2                        H.sub.5                                                          Ia.84 Cl     CH═C(Cl)--CO--N(CH.sub.3)--CH.sub.2 --CO--OC.sub.2                        H.sub.5                                                          Ia.85 CN     CH═C(Cl)--CO--NH--CH(CH.sub.3)--CO--OCH.sub.3                Ia.86 Cl     CH═C(Cl)--CO--NH--CH(CH.sub.3)--CO--OCH.sub.3                Ia.87 CN     CH═C(Cl)--CO--NH--CH(CH.sub.3)--CO--OC.sub.2 H.sub.5         Ia.88 Cl     CH═C(Cl)--CO--NH--CH(CH.sub.3)--CO--OC.sub.2 H.sub.5         Ia.89 CN     CH═C(Cl)--CO--NH--OCH.sub.3                                  Ia.90 Cl     CH═C(Cl)--CO--NH--OCH.sub.3                                  Ia.91 CN     CH═C(Cl)--CO--N(OCH.sub.3)--CH.sub.3                         Ia.92 Cl     CH═C(Cl)--CO--N(OCH.sub.3)--CH.sub.3                         Ia.93 CN     CH═C(Cl)--C(N--OCH.sub.3)--OCH.sub.3                         Ia.94 Cl     CH═C(Cl)--C(N--OCH.sub.3)--OCH.sub.3                         Ia.95 CN     CH═C(Cl)--C(N--OCH.sub.3)--OCH.sub.2 --CO--OCH.sub.3         Ia.96 Cl     CH═C(Cl)--C(N--OCH.sub.3)--OCH.sub.2 --CO--OCH.sub.3         Ia.97 CN     CH═C(Cl)--C(N--OCH.sub.3)--OCH.sub.2 --CO--OC.sub.2                       H.sub.5                                                          Ia.98 Cl     CH═C(Cl)--C(N--OCH.sub.3)--OCH.sub.2 --CO--OC.sub.2                       H.sub.5                                                          Ia.99 CN     CH═C(Cl)--C(N--OCH.sub.3)--OCH(CH.sub.3)--CO--OCH.sub.3      Ia.100                                                                              Cl     CH═C(Cl)--C(N--OCH.sub.3)--OCH(CH.sub.3)--CO--OCH.sub.3      Ia.101                                                                              CN     CH═C(Cl)--C(N--OCH.sub.3)--OCH(CH.sub.3)--CO--OC.sub.2                    H.sub.5                                                          Ia.102                                                                              Cl     CH═C(Cl)--C(N--OCH.sub.3)--OCH(CH.sub.3)--CO--OC.sub.2                    H.sub.5                                                          Ia.103                                                                              CN     CH═C(Cl)--C(N--OCH.sub.3)--OC(CH.sub.3).sub.2 --CO--OCH.s                 ub.3                                                             Ia.104                                                                              Cl     CH═C(Cl)--C(N--OCH.sub.3)--OC(CH.sub.3).sub.2 --CO--OCH.s                 ub.3                                                             Ia.105                                                                              CN     CH═C(Cl)--C(N--OCH.sub.3)--OC(CH.sub.3).sub.2 --CO--OC.su                 b.2 H.sub.5                                                      Ia.106                                                                              Cl     CH═C(Cl)--C(N--OCH.sub.3)--OC(CH.sub.3).sub.2 --CO--OC.su                 b.2 H.sub.5                                                      Ia.107                                                                              CN     OCH.sub.2 --C.tbd.CH                                             Ia.108                                                                              Cl     OCH.sub.2 --C.tbd.CH                                             Ia.109                                                                              CN     OCH(CH.sub.3)--C.tbd.CH                                          Ia.110                                                                              Cl     OCH(CH.sub.3)--C.tbd.CH                                          Ia.111                                                                              CN     OCH.sub.2 --CH═CH.sub.2                                      Ia.112                                                                              Cl     OCH.sub.2 --CH═CH.sub.2                                      Ia.113                                                                              CN     OCH(CH.sub.3)--CH═CH.sub.2                                   Ia.114                                                                              Cl     OCH(CH.sub.3)--CH═CH.sub.2                                   Ia.115                                                                              CN     OCH.sub.2 --CO--OCH.sub.3                                        Ia.116                                                                              Cl     OCH.sub.2 --CO--OCH.sub.3                                        Ia.117                                                                              CN     OCH.sub.2 --CO--OC.sub.2 H.sub.5                                 Ia.118                                                                              Cl     OCH.sub.2 --CO--OC.sub.2 H.sub.5                                 Ia.119                                                                              CN     OCH.sub.2 --CO--OCH.sub.2 --CO--OCH.sub.3                        Ia.120                                                                              Cl     OCH.sub.2 --CO--OCH.sub.2 --CO--OCH.sub.3                        Ia.121                                                                              CN     OCH.sub.2 --CO--OCH.sub.2 --CO--OC.sub.2 H.sub.5                 Ia.122                                                                              Cl     OCH.sub.2 --CO--OCH.sub.2 --CO--OC.sub.2 H.sub.5                 Ia.123                                                                              CN     OCH.sub.2 --CO--OCH(CH.sub.3)--CO--OCH.sub.3                     Ia.124                                                                              Cl     OCH.sub.2 --CO--OCH(CH.sub.3)--CO--OCH.sub.3                     Ia.125                                                                              CN     OCH.sub.2 --CO--OCH(CH.sub.3)--CO--OC.sub.2 H.sub.5              Ia.126                                                                              Cl     OCH.sub.2 --CO--OCH(CH.sub.3)--CO--OC.sub.2 H.sub.5              Ia.127                                                                              CN     OCH.sub.2 --CO--OC(CH.sub.3).sub.2 --CO--OCH.sub.3               Ia.128                                                                              Cl     OCH.sub.2 --CO--OC(CH.sub.3).sub.2 --CO--OCH.sub.3               Ia.129                                                                              CN     OCH.sub.2 --CO--OC(CH.sub.3).sub.2 --CO--OC.sub.2 H.sub.5        Ia.130                                                                              Cl     OCH.sub.2 --CO--OC(CH.sub.3).sub.2 --CO--OC.sub.2 H.sub.5        Ia.131                                                                              CN     OCH.sub.2 --CO--OCH.sub.2 --CH.sub.2 --OCH.sub.3                 Ia.132                                                                              Cl     OCH.sub.2 --CO--OCH.sub.2 --CH.sub.2 --OCH.sub.3                 Ia.133                                                                              CN     OCH(CH.sub.3)--CO--OCH.sub.3                                     Ia.134                                                                              Cl     OCH(CH.sub.3)--CO--OCH.sub.3                                     Ia.135                                                                              CN     OCH(CH.sub.3)--CO--OC.sub.2 H.sub.5                              Ia.136                                                                              Cl     OCH(CH.sub.3)--CO--OC.sub.2 H.sub.5                              Ia.137                                                                              CN     OCH(CH.sub.3)--CO--OCH.sub.2 --CO--OCH.sub.3                     Ia.138                                                                              Cl     OCH(CH.sub.3)--CO--OCH.sub.2 --CO--OCH.sub.3                     Ia.139                                                                              CN     OCH(CH.sub.3)--CO--OCH.sub.2 --CO--OC.sub.2 H.sub.5              Ia.140                                                                              Cl     OCH(CH.sub.3)--CO--OCH.sub.2 --CO--OC.sub.2 H.sub.5              Ia.141                                                                              CN     OCH(CH.sub.3)--CO--OCH(CH.sub.3)--CO--OCH.sub.3                  Ia.142                                                                              Cl     OCH(CH.sub.3)--CO--OCH(CH.sub.3)--CO--OCH.sub.3                  Ia.143                                                                              CN     OCH(CH.sub.3)--CO--OCH(CH.sub.3)--CO--OC.sub.2 H.sub.5           Ia.144                                                                              Cl     OCH(CH.sub.3)--CO--OCH(CH.sub.3)--CO--OC.sub.2 H.sub.5           Ia.145                                                                              CN     OCH(CH.sub.3)--CO--OCH.sub.2 --CH.sub.2 --OCH.sub.3              Ia.146                                                                              Cl     OCH(CH.sub.3)--CO--OCH.sub.2 --CH.sub.2 --OCH.sub.3              Ia.147                                                                              CN     NH--SO.sub.2 --CH.sub.3                                          Ia.148                                                                              Cl     NH--SO.sub.2 --CH.sub.3                                          Ia.149                                                                              CN     NH--SO.sub.2 --C.sub.2 H.sub.5                                   Ia.150                                                                              Cl     NH--SO.sub.2 --C.sub.2 H.sub.5                                   Ia.151                                                                              CN     NH--SO.sub.2 --CH.sub.2 --C.sub.6 H.sub.5                        Ia.152                                                                              Cl     NH--SO.sub.2 --CH.sub.2 --C.sub.6 H.sub.5                        Ia.153                                                                              CN     N(CH.sub.3)--SO.sub.2 --CH.sub.3                                 Ia.154                                                                              Cl     N(CH.sub.3)--SO.sub.2 --CH.sub.3                                 Ia.155                                                                              CN     N(C.sub.2 H.sub.5)--SO.sub.2 --CH.sub.3                          Ia.156                                                                              Cl     N(C.sub.2 H.sub.5)--SO.sub.2 --CH.sub.3                          Ia.157                                                                              CN     N(CH.sub.2 --C.sub.6 H.sub.5)--SO.sub.2 --CH.sub.3               Ia.158                                                                              Cl     N(CH.sub.2 --C.sub.6 H.sub.5)--SO.sub.2 --CH.sub.3               Ia.159                                                                              CN     N(SO.sub.2 --CH.sub.3).sub.2                                     Ia.160                                                                              Cl     N(SO.sub.2 --CH.sub.3).sub.2                                     ______________________________________                                    

Furthermore, particular preference is given to the substituted3-phenylisoxazolines of the formulae Ib and Ic, in particular to

the compounds Ib.1 to Ib.160, which differ from the correspondingcompounds Ia.1 to Ia.160 only in that R⁵ is chlorine: ##STR4## thecompounds Ic.1 to Ic.160, which differ from the corresponding compoundsIa.1 to Ia.160 only in that R⁵ is hydrogen: ##STR5## The3-phenylisoxazolines of the formula I are obtainable in a variety ofways, in particular by one of the following processes:

A) Reaction of a phenyl derivative II with hydroxylamine or one of itssalts, for example the hydrochloride or the hydrosulfate {cf. forexample M. A. P. Martins et al. in J. Heterocycl. Chem. 32 (1995), 739and 33 (1996), 1619, and Izv. Akad. Nauk, Ser. Khim. 1996 (5), p.1306/1307}: ##STR6## Z is oxygen, sulfur or --N(R⁹)--; L is hydrogen orhydroxysulfonyl.

In the case of R³ =hydrogen, at least some of the compounds II may bepresent in the tautomeric form IIa ##STR7## in which case they may alsobe employed in the form of their salts, in particular of the alkalimetal, alkaline earth metal or ammonium salts.

In general, the reaction is carried out in an inert organicsolvent/diluent, if desired in the presence of an acid or a base.

Suitable solvent systems are for example those mentioned below:

an organic acid such as acetic acid together with 0.5 to 10 times themolar amount--based on the amount of III--of an alkali metal or ammoniumsalt of the acid in question, i.e. for example sodium acetate orpotassium acetate;

mixtures of water and a lower alcohol such as methanol and ethanol (themixing ratio being chosen in such a way that the starting materialsdissolve) containing a base, for example potassium carbonate, or an acidsuch as hydrochloric acid;

mixtures of pyridine and a lower alcohol or an aromatic hydrocarbon suchas toluene. However, it is also possible to carry out the reaction inpure pyridine.

The reaction is generally carried out at from (-20)°C. to the boilingpoint of the reaction mixture in question, in particular at from 20° C.to the boiling point of the reaction mixture in question.

The starting materials II (or IIa) and III are usually employed inapproximately equimolar amounts, or one of the two components isemployed in excess, up to 2 times the molar amount of the othercomponent. Advantageously, the hydroxylamine (salt) is employed inexcess.

The process products I where R² =H can be converted in a manner knownper se, for example by alkylation or acetylation, into the compound Iwhere R² +H.

B) Reaction of a nitrile oxide of the formula V with a protected enolether VI {cf. for example Hunig et al., Chem. Ber. 119 (1986), 699-721}:##STR8## L² is a customary protecting group for hydroxyl, for examplemethyl, methylsulfonyl, benzyl or trimethylsilyl.

The nitrile oxides V are preferably prepared from the correspondinghydroxylamine derivatives IV (by elimination of hydrogen chloride usinga base) and subsequently reacted directly with VI without priorisolation from the reaction mixture.

Suitable bases are, for example, alkali metal carbonates such as sodiumcarbonate and potassium carbonate, alkali metal bicarbonates such aspotassium bicarbonate, alkali metal hydrides such as sodium hydride,alkali metal and alkaline earth metal hydroxides such as sodiumhydroxide, alkali metal alkoxides such as sodium methoxide and potassiumtert-butoxide, and amines such as triethylamine and pyridine.

The reaction can be carried out in a single phase in an organic solvent,for example in an aromatic hydrocarbon such as toluene, a halogenatedhydrocarbon such as methylene chloride, an ester such as ethyl acetate,an ether such as diethyl ether and tetrahydrofuran, a ketone such asacetone or a lower alcohol such as ethanol. Mixtures of ketone and wateror alcohol and water can also be employed.

However, in particular when using an alkali metal hydroxide as base, itis advantageous to carry out the reaction in a two-phase solvent mixtureof water and a solvent that is only poorly miscible with water, if atall, for example an aromatic hydrocarbon such as toluene, an ester suchas ethyl acetate or an ether such as diethyl ether.

The amount of base is of minor importance.

For the preparation of IV see, for example, Liu et al., J. Org. Chem. 45(1980), 3916-3918.

Unless stated otherwise, all of the processes described above areadvantageously carried out at atmospheric pressure or under theautogenous pressure of the reaction mixture in question.

Work-up of the reaction mixtures is usually carried out by methods knownper se, for example by diluting the reaction solution with water andsubsequently isolating the product by filtration, crystallization orsolvent extraction, or by removing the solvent, partitioning the residuein a mixture of water and a suitable organic solvent and work-up of theorganic phase to afford the product.

The 3-phenylisoxazolines I are usually preparable by one of theabovementioned synthesis processes. However, for economical or technicalreasons it may be more advantageous to prepare some of the compounds Ifrom similar 3-phenylisoxazolines which differ in particular in themeaning of the radicals R⁷ and/or R⁸, employing a procedure known perse, for example ester hydrolysis, esterification, amidation,acetalization, acetyl hydrolysis, a condensation reaction, aWittig-reaction, Peterson-olefination, etherification, alkylation,oxidation or reduction.

The substituted 3-phenylisoxazolines I may be obtained as isomermixtures in the preparation. If desired, these mixtures can be separatedinto the pure isomers using the customary methods for this purpose, suchas crystallization or chromatography, including chromatography over anoptically active adsorbate. Pure optically active isomers can beadvantageously prepared, for example, from suitable optically activestarting materials.

Agriculturally useful salts of the compounds I can be formed by reactionwith a base of the appropriate cation, preferably an alkali metalhydroxide or alkali metal hydride, or by reaction with an acid of theappropriate anion, preferably hydrochloric acid, hydrobromic acid,sulfuric acid, phosphoric acid or nitric acid.

Salts of I, where the metal ion is not an alkali metal ion, can also beprepared by cation exchange of the corresponding alkali metal salt in aconventional manner, similarly ammonium, phosphonium, sulfonium andsulfoxonium salts by means of ammonia, phosphonium, sulfonium orsulfoxonium hydroxides.

The compounds I and their agriculturally useful salts are suitable, bothin the form of isomer mixtures and in the form of the pure isomers, asherbicides. The herbicidal compositions comprising I control vegetationon non-crop areas very efficiently, especially at high rates ofapplication. They act against broad-leaved weeds and grass weeds incrops such as wheat, rice, maize, soya and cotton without causing anysignificant damage to the crop plants. This effect is mainly observed atlow rates of application.

Depending on the application method in question, the compounds I, orherbicidal compositions comprising them, can additionally be employed ina further number of crop plants for eliminating undesired plants.Examples of suitable crops are the following: Allium cepa, Ananascomosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec.altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassicanapus var. napobrassica, Brassica rapa var. silvestris, Camelliasinensis, Carthamus tinctorius, carya illinoinensis, Citrus limon,Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica),Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis,Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum,Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Heveabrasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglansregia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum,Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotianatabacum (N.rustica), Olea europaea, oryza sativa, Phaseolus lunatus,Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunusavium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinuscommunis, Saccharum officinarum, Secale cereale, Solanum tuberosum,Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense,Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zeamays.

In addition, the compounds I may also be used in crops which toleratethe action of herbicides owing to breeding, including geneticengineering methods.

The compounds I, or the herbicidal compositions comprising them, can beused for example in the form of ready-to-spray aqueous solutions,powders, suspensions, also highly-concentrated aqueous, oily or othersuspensions or dispersions, emulsions, oil dispersions, pastes, dusts,materials for scattering, or granules, by means of spraying, atomizing,dusting, scattering or watering. The use forms depend on the intendeduses; in any case, they should guarantee the finest possibledistribution of the active ingredients according to the invention.

Suitable as inert auxiliaries are essentially the following: mineral oilfractions of medium to high boiling point, such as kerosene and dieseloil, furthermore coal tar oils and oils of vegetable or animal origin,aliphatic, cyclic and aromatic hydrocarbons, eg. paraffin,tetrahydronaphthalene, alkylated naphthalenes and their derivatives,alkylated benzenes and their derivatives, alcohols such as methanol,ethanol, propanol, butanol and cyclohexanol, ketones such ascyclohexanone, strongly polar solvents, eg. amines such asN-methylpyrrolidone, and water.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water. To prepare emulsions, pastes or oil dispersions, thesubstituted 3-phenylisoxazolines I, either as such or dissolved in anoil or solvent, can be homogenized in water by means of a wetting agent,tackifier, dispersant or emulsifier. Alternatively, it is possible toprepare concentrates comprising active ingredient, wetting agent,tackifier, dispersant or emulsifier and, if desired, solvent or oil,which are suitable for dilution with water.

Suitable surfactants are the alkali metal salts, alkaline earth metalsalts and ammonium salts of aromatic sulfonic acids, eg. ligno-,phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fattyacids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ethersulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta-and octadecanols, and also of fatty alcohol glycol ethers, condensatesof sulfonated naphthalene and its derivatives with formaldehyde,condensates of naphthalene or of the naphthalenesulfonic acids withphenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylatedisooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenylpolyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol,fatty alcohol/ethylene oxide condensates, ethoxylated castor oil,polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, laurylalcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite wasteliquors or methylcellulose.

Powders, materials for scattering and dusts can be prepared by mixing orgrinding the active ingredients together with a solid carrier.

Granules, eg. coated granules, impregnated granules and homogeneousgranules, can be prepared by binding the active ingredients to solidcarriers. Solid carriers are mineral earths such as silicas, silicagels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess,clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfateand magnesium oxide, ground synthetic materials, fertilizers such asammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, andproducts of vegetable origin, such as cereal meal, tree bark meal, woodmeal and nutshell meal, cellulose powders, or other solid carriers.

The concentrations of the active compounds I in the ready-to-usepreparations can be varied within wide ranges. In general, theformulations comprise approximately from 0.001 to 98% by weight,preferably 0.01 to 95% by weight, of at least one active compound. Theactive compounds are employed in a purity of from 90% to 100%,preferably 95% to 100% (according to NMR spectrum).

The following formulation examples illustrate the preparation of suchpreparations:

I. 20 parts by weight of the compound No. 3 are dissolved in a mixturecomposed of 80 parts by weight of alkylated benzene, 10 parts by weightof the adduct of from 8 to 10 mol of ethylene oxide to 1 mol of oleicacid N-monoethanolamide, 5 parts by weight of calciumdodecylbenzenesulfonate and 5 parts by weight of the adduct of 40 mol ofethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000parts by weight of water and finely distributing it therein gives anaqueous dispersion which comprises 0.02% by weight of the activeingredient.

II. 20 parts by weight of the compound No. 4 are dissolved in a mixturecomposed of 40 parts by weight of cyclohexanone, 30 parts by weight ofisobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxideto 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into100,000 parts by weight of water and finely distributing it thereingives an aqueous dispersion which comprises 0.02% by weight of theactive ingredient.

III. 20 parts by weight of the active ingredient No. 12 are dissolved ina mixture composed of 25 parts by weight of cyclohexanone, 65 parts byweight of a mineral oil fraction of boiling point 210 to 280° C. and 10parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol ofcastor oil. Pouring the solution into 100,000 parts by weight of waterand finely distributing it therein gives an aqueous dispersion whichcomprises 0.02% by weight of the active ingredient.

IV. 20 parts by weight of the active ingredient No. 13 are mixedthoroughly with 3 parts by weight of sodiumdiisobutylnaphthalene-α-sulfonate, 17 parts by weight of the sodium saltof a lignosulfonic acid from a sulfite waste liquor and 60 parts byweight of pulverulent silica gel, and the mixture is ground in a hammermill. Finely distributing the mixture in 20,000 parts by weight of watergives a spray mixture which comprises 0.1% by weight of the activeingredient.

V. 3 parts by weight of the active ingredient No. 14 are mixed with 97parts by weight of finely divided kaolin. This gives a dust whichcomprises 3% by weight of the active ingredient.

VI. 20 parts by weight of the active ingredient No. 16 are mixedintimately with 2 parts by weight of calcium dodecylbenzenesulfonate, 8parts by weight of fatty alcohol polyglycol ether, 2 parts by weight ofthe sodium salt of a phenol/urea/formaldehyde condensate and 68 parts byweight of a paraffinic mineral oil. This gives a stable oily dispersion.

VII. 1 part by weight of the compound No. 17 is dissolved in a mixturecomposed of 70 parts by weight of cyclohexanone, 20 parts by weight ofethoxylated isooctylphenol and 10 parts by weight of ethoxylated castoroil. This gives a stable emulsion concentrate.

VIII. 1 part by weight of the compound No. 12 is dissolved in a mixturecomposed of 80 parts by weight of cyclohexanone and 20 parts by weightof Wettol® EM 31 (=nonionic emulsifier based on ethoxylated castor oil;BASF AG). This gives a stable emulsion concentrate.

The active ingredients I or the herbicidal compositions can be appliedpre- or post-emergence. If the active ingredients are less welltolerated by certain crop plants, application techniques may be used inwhich the herbicidal compositions are sprayed, with the aid of thespraying equipment, in such a way that as far as possible they do notcome into contact with the leaves of the sensitive crop plants, whilethe active ingredients reach the leaves of undesired plants growingunderneath, or the bare soil surface (post-directed, lay-by).

The rates of application of active ingredient I are from 0.001 to 3.0,preferably 0.01 to 1.0, kg/ha of active substance (a.s.), depending onthe control target, the season, the target plants and the growth stage.

To widen the spectrum of action and to achieve synergistic effects, thesubstituted 3-phenylisoxazolines I may be mixed with a large number ofrepresentatives of other herbicidal or growth-regulating activeingredients and then applied concomitantly. Suitable components formixtures are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles,amides, aminophosphoric acid and its derivatives, aminotriazoles,anilides, (het)aryloxyalkanoic acids and their derivatives, benzoic acidand its derivatives, benzothiadiazinones,2-(hetaroyl/aroyl)-1,3-cyclohexanediones, hetaryl aryl ketones,benzylisoxazolidinones, meta-CF₃ -phenyl derivatives, carbamates,quinolinecarboxylic acid and its derivatives, chloroacetanilides,cyclohexane-1,3-dione derivatives, diazines, dichloropropionic acid andits derivatives, dihydrobenzofurans, dihydrofuran-3-ones,dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls,halocarboxylic acids and their derivatives, ureas, 3-phenyluracils,imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides,oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionicesters, phenylacetic acid and its derivatives, 2-phenylpropionic acidand its derivatives, pyrazoles, phenylpyrazoles, pyridazines,pyridinecarboxylic acid and its derivatives, pyrimidyl ethers,sulfonamides, sulfonylureas, triazines, triazinones, triazolinones,triazolecarboxamides and uracils.

It may furthermore be advantageous to apply the compounds I, alone or incombination with other herbicides, in the form of a mixture with othercrop protection agents, for example together with agents for controllingpests or phytopathogenic fungi or bacteria. Also of interest is themiscibility with mineral salt solutions, which are employed for treatingnutritional and trace element deficiencies. Non-phytotoxic oils and oilconcentrates may also be added.

PREPARATION EXAMPLES Example 1 (Compound No. 1)

4-Chloro-3-(4'-chloro-2',5'-difluorophenyl)-5-hydroxy-5-trifluoromethylisoxazoline

20.93 g of hydroxylamine-O-sulfonic acid, 55 g of sodium bicarbonate and21 g of sodium hydrosulfide hydrate were added in succession to 50 g of2-chloro-1-(4'-chloro-2',5'-difluorophenyl)-4,4,4-trifluorobuta-1,3-dionein 300 ml of ethanol and 80 ml of water. The reaction mixture wasstirred for 17 hours and then concentrated under reduced pressure. Theresidue was taken up in 200 ml of water and 200 ml of ethyl acetate. Theresulting mixture was subsequently mixed with 50 ml of dilutehydrochloric acid. The organic phase was then separated off, dried oversodium sulfate and finally concentrated. The oily crude product waspurified by silica gel column chromatography (eluent:toluene/cyclohexane=1:1). Yield: 16 g.

Intermediate 1.1

1-(4'-Chloro-2',5'-difluorophenyl)-4,4,4-trifluorobuta-1,3-dione

At 5° C., 21.5 g of a 30% strength by weight solution of sodiummethoxide in methanol was added dropwise to a mixture of 22.5 g of2,5-difluoro-4-chloroacetophenone, 15.17 g of methyl trifluoroacetateand 200 ml of diethyl ether. The reaction mixture was stirred at about20° C. for 17 hours, and the pH was then adjusted to 3 by the additionof 10% strength hydrochloric acid. The organic phase was subsequentlyseparated off, dried over sodium sulfate and finally concentrated underreduced pressure. The crude product was purified by stirring withpetroleum ether and filtering off the undissolved product of value.Yield: 22 g; m.p.: 61-63° C.

Intermediate 1.2

2-Chloro-1-(4'-chloro-2',5'-difluorophenyl)-4,4,4-trifluorobuta-1,3-dione

At about 20° C., 6 ml of sulfuryl chloride were added dropwise to 18 gof 1-(4 '-chloro-2',5'-difluorophenyl)-4,4,4-trifluorobuta-1,3-dione in200 ml of trichloromethane. The mixture was subsequently initiallystirred for 17 hours without heating and then for a further 2 hours at40° C. The low-boiling components were finally distilled off. Yield: 22g; oil.

Example 2 (Compound No. 2)

4-Chloro-3-(4'-chloro-2',5'-difluorophenyl)-5-(methylcarbonyloxy)-5-trifluoromethylisoxazoline

One drop of concentrated sulfuric acid was added to 3.2 g of4-chloro-3-(4'-chloro-2',5'-difluorophenyl)-5-hydroxy-5-trifluoromethylisoxazolinein 45 ml of acetic anhydride. The mixture was subsequently brieflyheated to 160° C. After cooling, the reaction mixture was thenconcentrated under reduced pressure. The oily crude product was purifiedby silica gel chromatography (eluent: methylene chloride). Yield: 2.5 g;oil.

Example 3 (Compound No. 3)

4-Chloro-3-(4'-chloro-2'-fluoro-5'-methylphenyl)-5-hydroxy-5-trifluoromethylisoxazoline

30.7 g of sodium acetate and 26 g of hydroxylamine hydrochloride wereadded to 107.8 g of2-chloro-1-(4'-chloro-2'-fluoro-5'-methylphenyl-4,4,4-trifluorobuta-1,3-dionein 300 ml of glacial acetic acid, and the mixture was then stirred atabout 20° C. for 17 hours. The mixture was then concentrated and theresidue was taken up in 500 ml of ethyl acetate. The organic phase waswashed with 200 ml of water, dried over sodium sulfate and finallyconcentrated. For purification, the crude product was stirred withpetroleum ether. The solid components were separated off. Yield: 34 g;m.p.: 90-91° C. Chromatographic separation of the filtrate over silicagel (eluent:toluene/dichloromethane=1:1) gave a further 32 g of theproduct of value. Total yield: 66 g.

Intermediate 3.1

4-Chloro-2-fluoro-5-methylacetophenone

At 60° C., 157 g of acetyl chloride were added dropwise to a mixture of250 g of 2-chloro-4-fluorotoluene and 267 g of aluminum chloride. Thereaction mixture was stirred at 120° C. for 2 hours and then, whilestill at 100° C., poured onto 2 l of an ice/water mixture. 180 ml ofconcentrated hydrochloric acid were subsequently stirred into theresulting mixture. The product was then extracted using three times 200ml of dichloromethane. The organic phase was then washed with 200 ml ofwater, dried over sodium sulfate and finally concentrated. Yield: 290 g;oil.

Intermediate 3.2

2-Chloro-1-(4'-chloro-2'-fluoro-5'-methylphenyl-4,4,4-trifluorobuta-1,3-dione

33 ml of sulfuryl chloride were added dropwise to 96.1 g of1-(4'-chloro-2'-fluoro-5'-methylphenyl)-4,4,4-trifluorobuta-1,3-dione(prepared similarly to intermediate 1.1) in 300 ml of dichloromethane.The mixture was subsequently stirred at about 20° C. for 17 hours. Thereaction mixture was then concentrated under reduced pressure. Yield:108 g; oil.

Example 4 (Compound No. 4)

4-Chloro-3-(5'-carboxyl-4'-chloro-2'-fluorophenyl)-5-hydroxy-5-trifluoromethylisoxazoline

2.2 g of sodium dichromate dihydrate were added to 1.7 g of4-chloro-3-(4'-chloro-2'-fluoro-5'-methylphenyl)-5-hydroxy-5-trifluoromethylisoxazolinein 25 ml of concentrated sulfuric acid whereupon the reactiontemperature rose to 40° C. The mixture was subsequently stirred for afurther 5 hours at about 20° C., and a further 0.6 g of sodiumdichromate dihydrate was added. Stirring was then continued for afurther 14 hours at about 20° C., and the reaction mixture was thenpoured into 100 ml of ice-water. The product was extracted from theaqueous phase using 100 ml of methylene chloride. The organic phase waswashed with 100 ml of water, dried over sodium sulfate and finallyconcentrated. Yield: 1.2 g; oil.

Example 5 (Compound No. 5)

4-Chloro-3-(4'-chloro-2'-fluoro-5'-methylphenyl)-5-(methylcarbonyloxy)-5-trifluoromethylisoxazoline

A solution of 0.64 g of4-chloro-3-(5'-carboxyl-4'-chloro-2'-fluorophenyl)-5-hydroxy-5-trifluoromethylisoxazolinein 25 ml of acetic anhydride was initially stirred for 18 hours at 60°C., and then for a further 3 hours at 120° C. The solvent wassubsequently distilled off, giving an oily residue from which theproduct of value crystallized out. The crystals were filtered off andwashed with petroleum ether. Yield: 400 mg.

Example 6 (Compound No. 7)

3-(4'-Chlorophenyl)-4-chloro-5-hydroxy-5-trifluoromethylisoxazoline

At 0° C., 0.87 g of hydroxylamine-O-sulfonic acid was added to a mixtureof 2.2 g of 2-chloro-1-(4'-chlorophenyl)-4,4,4-trifluorobuta-1,3-dione,10 ml of methanol and 10 ml of water. The reaction mixture was stirredfor 17 hours, and initially 2 g of sodium bicarbonate and then 0.5 g ofsodium hydrosulfide were added. Byproducts were precipitated by theaddition of 50 ml of water and then separated off. The solution thatremained was admixed with 10 ml of dilute hydrochloric acid. The productwas subsequently extracted using 100 ml of ethyl acetate. The organicphase was washed with 50 ml of water, dried over sodium sulfate andfinally concentrated. For purification, the crude product was stirredwith a mixture of diethyl ether and cyclohexane (1:1). The resultinglight-yellow solid was separated off. Yield: 0.84 g; m.p.: 126-127° C.

Intermediate 6.1

1-(4'-Chlorophenyl)-4,4,4-trifluorobuta-1,3-dione

At 5° C., 107.8 g of a 30% strength by weight solution of sodiummethoxide in methanol were added dropwise to a mixture of 92 g of4-chloroacetophenone, 800 ml of diethyl ether and 77 g of methyltrifluoroacetate. The reaction mixture was stirred at about 20° C. for17 hours and the pH was then adjusted to 3 by the addition of 10%strength hydrochloric acid. The organic phase was subsequently separatedoff, dried over sodium sulfate and finally concentrated under reducedpressure. The crude product was purified by stirring with petroleumether and filtering off the undissolved fraction. Yield: 105 g; m.p.:56-57° C.

Intermediate 6.2

2-Chloro-1-(4'-chlorophenyl)-4,4,4-trifluorobuta-1,3-dione

0.86 ml of sulfuryl chloride was added to 2.5 g of1-(4'-chlorophenyl)-4,4,4-trifluorobuta-1,3-dione in 15 ml oftrichloromethane. The reaction mixture was stirred for 3 hours and thenconcentrated under reduced pressure. Yield: 2.8 g; oil.

Example 7 (Compound No. 8)

4-Chloro-3-(4'-chloro-3'-nitrophenyl)-5-hydroxy-5-trifluoromethylisoxazoline

At 5° C., 1.81 ml of a mixture of 0.46 ml of 98% strength nitric acidand 1.35 ml of concentrated sulfuric acid were added dropwise to 2.4 gof 3-(4'-chlorophenyl)-4-chloro-5-hydroxy-5-trifluoromethylisoxazolinein 20 ml of concentrated sulfuric acid. The reaction mixture was stirredat 5° C. for 1.5 hours and then poured into 300 ml of ice-water. Theorganic phase was subsequently separated off, dried over sodium sulfateand finally concentrated. Yield: 2.5 g.

In addition to the physical data of the compounds I described above,further 3-phenylisoxazolines according to the invention which were alsoprepared or are preparable by one of the processes described are listedin Table 2 below:

                                      TABLE 2                                     __________________________________________________________________________     ##STR9##                                                                     I {X = O; R.sup.1 = CF.sub.3 ; R.sup.3, R.sup.6 = H;                            R.sup.7 in position α;                                                  R.sup.8 in position β}                                                                                physical                                       No.                                                                              R.sup.2 R.sup.4                                                                         R.sup.5                                                                         R.sup.7                                                                          R.sup.8      data                                           __________________________________________________________________________     1 H       Cl                                                                              F Cl F            oil                                             2 CO--CH.sub.3                                                                          Cl                                                                              F Cl F            oil                                             3 H       Cl                                                                              F Cl CH.sub.3     95-97° C.                                4 H       Cl                                                                              F Cl COOH         oil                                             5 CO--CH.sub.3                                                                          Cl                                                                              F Cl CH.sub.3     crystalline                                     6 H       Cl                                                                              H Cl NO.sub.2     oil                                             7 H       Cl                                                                              H Cl H            126-127° C.                              8 H       Cl                                                                              F Cl CO--NH--OCH.sub.2 C.sub.6 H.sub.5                                                          71-75° C.                                9 H       Cl                                                                              F F  H            oil                                            10 H       Cl                                                                              H Cl CH.sub.3     oil                                            11 H       Cl                                                                              F Cl CH.sub.2 Cl  oil                                            12 H       Cl                                                                              F Cl CO--OC.sub.2 H.sub.5                                                                       oil                                            13 H       Cl                                                                              F Cl CHO          oil                                            14 H       Cl                                                                              F Cl CO--OCH.sub.3                                                                              88-90° C.                               15 H       Cl                                                                              F Cl CO--OCH(CH.sub.3).sub.2                                                                    oil                                            16 H       Cl                                                                              F Cl CO--OCH(CH.sub.3)CO--OCH.sub.3                                                             oil                                            17 H       Cl                                                                              F Cl OCH.sub.3    oil                                            18 CO--C.sub.2 H.sub.5                                                                   Cl                                                                              F Cl CO--OC.sub.2 H.sub.5                                                                       oil                                            19 H       Cl                                                                              F Cl CO--NH--OCH.sub.3                                                                          oil                                            20 H       Cl                                                                              Cl                                                                              Cl CH.sub.3     92-93° C.                               21 H       Cl                                                                              Cl                                                                              Cl CH.sub.2 Cl  oil                                            22 H       Cl                                                                              Cl                                                                              Cl CHO          130-131° C.                             23 CO--CH.sub.3                                                                          Cl                                                                              F Cl CO--OC.sub.2 H.sub.5                                                                       oil                                            24 CO--CH(CH.sub.3).sub.2                                                                Cl                                                                              F Cl CO--OC.sub.2 H.sub.5                                                                       oil                                            25 H       Cl                                                                              Cl                                                                              Cl CO--OCH.sub.3                                                                              oil                                            26 H       Cl                                                                              Cl                                                                              Cl CH═C(Cl)CO--OC.sub.2 H.sub.5                                                           oil                                            27 H       Cl                                                                              Cl                                                                              Cl CO--OC.sub.2 H.sub.5                                                                       oil                                            28 H       Cl                                                                              Cl                                                                              Cl CH.sub.2 OH  103-105° C.                             29 H       Cl                                                                              Cl                                                                              Cl CH═N--OCH.sub.3                                                                        97-99° C.                               30 H       Cl                                                                              Cl                                                                              Cl CH═N--OC.sub.2 H.sub.5                                                                 78-82° C.                               __________________________________________________________________________

Use Examples

The herbicidal activity of the substituted 3-phenylisoxazolines I wasdemonstrated by the following greenhouse experiments:

The culture containers used were plastic flowerpots containing loamysand with approximately 3.0% of humus as the substrate. The seeds of thetest plants were sown separately for each species.

In the pre-emergence treatment, the active compounds, which had beensuspended or emulsified in water, were applied directly after sowing bymeans of finely distributing nozzles. The containers were irrigatedgently to promote germination and growth and subequently covered withtransparent plastic hoods until the plants had rooted. This cover causesuniform germination of the test plants, unless this was adverselyaffected by the active compounds.

For the post-emergence treatment, the test plants were first grown to aheight of 3 to 15 cm, depending on the growth habit, and only thentreated with the active compounds which had been suspended or emulsifiedin water. For this purpose, the test plants were either sown directlyand grown in the same containers, or they were first grown separately asseedlings and transplanted into the test containers a few days prior tothe treatment. The rate of application for the post-emergence treatmentwas 31.2 or 15.6 g/ha of a.s. (active substance).

Depending on the species, the plants were kept at 10-25° C. or 20-35° C.The test period extended over 2 to 4 weeks. During this time, the plantswere tended, and their response to the individual treatments wasevaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means noemergence of the plants, or complete destruction of at least theabove-ground parts, and 0 means no damage, or normal course of growth.

The plants used in the greenhouse experiments were of the followingspecies:

    ______________________________________                                        Scientific name    Common name                                                ______________________________________                                        Galium aparine     catchweed bedstraw                                         Ipomoea species    morning glory                                              Setaria faberii    giant foxtail                                              Sinapis alba       white mustard                                              Solanum nigrum     black nightshade                                           ______________________________________                                    

At application rates of 31.2 and 15.6 g/ha of a.s., compound no. 12showed very good herbicidal activity against the abovementioned harmfulgrasses or broad-leaved plants when applied by the post-emergencemethod.

What is claimed is:
 1. A substituted 3-phenylisoxazoline of the formulaI ##STR10## where: X is oxygen, sulfur or --N(R⁹)--;R¹ is C₁ -C₄-haloalkyl; R² is hydrogen, C₁ -C₆ -alkyl, (C₁ -C₆ -alkyl)carbonyl, C₁-C₆ -alkylsulfonyl, C₂ -C₆ -alkenyl, (C₂ -C₆ -alkenyl)carbonyl, C₂ -C₆-alkynyl or (C₂ -C₆ -alkynyl)carbonyl, where the 7 last-mentionedradicals may, optionally, carry 1 to 3 radicals, in each case selectedfrom the group consisting of halogen, C₁ -C₆ -alkoxy, C₁ -C₆-alkylamino, di(C₁ -C₆ -alkyl)amino, C₁ -C₆ -alkoxyimino, phenyl,CO--OR¹⁰ and CO--N(R¹ l)--R¹² ; R³ is hydrogen; R⁴ is halogen; R⁵ ishydrogen or halogen; R⁶ is hydrogen; R⁷ is cyano or halogen; R⁸ is1)hydrogen, hydroxyl, mercapto, cyano, nitro, halogen, C₁ -C₆ -alkyl, C₁-C₆ -haloalkyl, C₁ -C₆ -haloalkoxy, C₁ -C₆ -haloalkylthio, C₁ -C₆-alkylthio-(C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆ -alkyl)iminooxycarbonyl, C₁-C₆ -alkoxy-C₁ -C₆ -alkyl, C₁ -C₆ -alkoxyamino-C₁ -C₆ -alkyl, C₁ -C₆-alkoxy-C₁ -C₆ -alkylamino-C₁ -C₆ -alkyl, 2) C₁ -C₆ -alkoxy, C₁ -C₆-alkylthio, C₃ -C₆ -cycloalkoxy, C₃ -C₆ -cycloalkylthio, C₂ -C₆-alkenyloxy, C₂ -C₆ -alkenylthio, C₂ -C₆ -alkynyloxy, C₂ -C₆-alkynylthio, (C₁ -C₆ -alkyl)carbonyloxy, (C₁ -C₆ -alkyl)carbonylthio,(C₁ -C₆ -alkoxy)carboxyloxy, (C₂ -C₆ -alkenyl)carbonyloxy, (C₂ -C₆-alkenyl)carbonylthio, (C₂ -C₆ -alkynyl)carbonyloxy, (C₂ -C₆-alkynyl)carbonylthio, C₁ -C₆ -alkylsulfonyloxy or C₁ -C₆-alkylsulfonyl, where each of the 17 last-mentioned radicals may,optionally, carry one to three substituents, in each case selected fromthe group consisting ofhalogen, nitro, cyano, hydroxyl, C₃ -C₆-cycloalkyl, C₁ -C₆ -alkoxy, C₃ -C₆ -cycloalkoxy, C₃ -C₆ -alkenyloxy, C₃-C₆ -alkynyloxy, C₁ -C₆ -alkoxy-C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, C₁-C₆ -alkylsulfinyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆ -alkylideneaminooxy,oxo, ═N--OR¹⁸, the phenyl, phenoxy or phenylsulfonyl group, which may beunsubstituted or may carry one to three substituents, in each caseselected from the group consisting of halogen, nitro, cyano, C₁ -C₆-alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy and (C₁ -C₆ -alkoxy)carbonyl,a group --CO--R¹⁹, --CO--OR¹⁹, --CO--SR¹⁹, --CO--N(R¹⁹)R²⁰, --OCO--R¹⁹,--OCO--OR¹⁹, --OCO--SR¹⁹, --OCO--N(R¹⁹)R²⁰ or --N(R¹⁹)--R²⁰, 3)--CO--R²², --CS--R²², --C(NR²³)--R²², --C(R²²)(Z¹ R²⁴)(Z² R²⁵), where Z¹and Z² are each oxygen or sulfur, --C(R²²)═C(R²⁶)--CN,--C(R²²)═C(R²⁶)--CO--R²⁷, --CH(R²²)--CH(R²⁶)--CO--R²⁷,--C(R²²)═C(R²⁶)--CH₂ --CO--R²⁷, --C(R²²)═C(R²⁶)--C(R²⁸)═C(R²⁹)--CO--R²⁷,--C(R²²)═C(R²⁶)--CH₂ --CH(R³⁰)--CO--R²⁷, --CO--OR³¹, --CO--SR³¹,--CO--N(R³¹)--OR¹⁸, --C.tbd.C--CO--N(R³¹)--OR¹⁸,--C.tbd.C--CS--N(R³¹)--OR¹⁸, --C(R²²)═C(R²⁶)--CO--N(R³¹)--OR¹⁸,--C(R²²)═C(R²⁶)--CS--N(R³¹)--OR¹⁸, --C(R²²)═C(R²⁶)--C(R²¹)═N--OR¹⁸,--C(R²¹)═N--OR¹⁸, --C.tbd.C--C(R²¹)═N--OR¹⁸, --C(Z¹ R²⁴)(Z² R²⁵)--OR³¹,--C(Z¹ R²⁴)(Z² R²⁵)--SR³¹, --C(Z¹ R²⁴)(Z² R²⁵)--N(R³²)R³³, --N(R³²)R³³or --CON(R³²)R³³ ; R⁹, R¹⁰ and R¹² independently of one another are eachhydrogen, C₁ -C₆ -alkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆-alkynyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆-alkyl, (C₃ -C₆ -alkenyloxy)carbonyl-C₁ -C₆ -alkyl, phenyl or phenyl-C₁-C₆ -alkyl, where the phenyl group and the phenyl ring of thephenylalkyl group may be unsubstituted or may carry one to threeradicals, in each case selected from the group consisting of halogen,nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy and (C₁-C₆ -alkyl)carbonyl; R¹¹ is hydrogen, hydroxyl, C₁ -C₆ -alkyl, C₃ -C₆-cycloalkyl, C₁ -C₆ -alkoxy, (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkoxy, C₃-C₆ -alkenyl or C₃ -C₆ -alkenyloxy; R²² is hydrogen, cyano, C₁ -C₆-alkyl, C₁ -C₆ -haloalkyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, C₃ -C₆-cycloalkyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl or (C₁ -C₆ -alkoxy)carbonyl;R²³ is hydrogen, hydroxyl, C₁ -C₆ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆-alkynyl, C₃ -C₇ -cycloalkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy-C₁ -C₆-alkyl, C₁ -C₆ -alkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆ -alkynyloxy, C₃ -C₆-cycloalkoxy, C₅ -C₇ -cycloalkenyloxy, C₁ -C₆ -haloalkoxy, C₃ -C₆-haloalkenyloxy, hydroxy-C₁ -C₆ -alkoxy, cyano-C₁ -C₆ -alkoxy, C₃ -C₆-cycloalkyl-C₁ -C₆ -alkoxy, C₁ -C₆ -alkoxy-C₁ -C₆ -alkoxy, C₁ -C₆-alkoxy-C₃ -C₆ -alkenyloxy, (C₁ -C₆ -alkyl)carbonyloxy, (C₁ -C₆-haloalkyl)carbonyloxy, (C₁ -C₆ -alkyl)carbamoyloxy, (C₁ -C₆-haloalkyl)carbamoyloxy, (C₁ -C₆ -alkyl)carbonyl-C₁ -C₆ -alkyl, (C₁ -C₆-alkyl)carbonyl-C₁ -C₆ -alkoxy, (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkyl,(C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio-C₁ -C₆-alkoxy, di(C₁ -C₆ -alkyl)amino-C₁ -C₆ -alkoxy, phenyl which may itselfcarry one to three substituents, in each case selected from the groupconsisting of cyano, nitro, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl,C₂ -C₆ -alkenyl, C₁ -C₆ -alkoxy and (C₁ -C₆ -alkoxy)carbonyl, phenyl-C₁-C₆ -alkoxy, phenyl-C₃ -C₆ -alkenyloxy or phenyl-C₃ -C₆ -alkynyloxy,where in each case one or two methylene groups of the hydrocarbon chainsmay be replaced by --O--, --S-- or --N(C₁ -C₆ -alkyl)-, and where eachphenyl ring may be unsubstituted or may carry one to three substituents,in each case selected from the group consisting of cyano, nitro,halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₂ -C₆ -alkenyl, C₁ -C₆-alkoxy and (C₁ -C₆ -alkoxy)carbonyl, heterocyclyl, heterocyclyl-C₁ -C₆-alkoxy, heterocyclyl-C₃ -C₆ -alkenyloxy or heterocyclyl-C₃ -C₆-alkynyloxy, where in each case one or two methylene groups of thehydrocarbon chains may be replaced by --O--, --S-- or --N(C₁ -C₆-alkyl)-, and where each heterocycle may have 3 to 7 members and may besaturated, unsaturated or aromatic and contains 1 to 4 heteroatomsselected from the group consisting of two oxygen atoms, two sulfur atomsand 4 nitrogen atoms, and is either unsubstituted or itself carries oneto three substituents, in each case selected from the group consistingof cyano, nitro, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₂ -C₆-alkenyl, C₁ -C₆ -alkoxy and (C₁ -C₆ -alkoxy)carbonyl, or --N(R³⁵)R³⁶,where R³⁵ and R³⁶ are each hydrogen, C₁ -C₆ -alkyl, C₃ -C₆ -alkenyl, C₃-C₆ -alkynyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy-C₁-C₆ -alkyl, (C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆ -alkoxy)carbonyl, (C₁ -C₆-alkoxy)carbonyl-C₁ -C₆ -alkyl, (C₁ -C₆ -alkoxy)carbonyl-C₂ -C₆-alkenyl, where the alkenyl chain may additionally carry one to threehalogen and/or cyano radicals, or phenyl which may be unsubstituted ormay itself carry one to three substituents, in each case selected fromthe group consisting of cyano, nitro, halogen, C₁ -C₆ -alkyl, C₁ -C₆-haloalkyl, C₃ -C₆ -alkenyl, C₁ -C₆ -alkoxy and (C₁ -C₆-alkoxy)carbonyl, or where R³⁵ and R³⁶ together with the common nitrogenatom form a saturated or unsaturated 4- to 7-membered azaheterocyclewhich in addition to carbon ring members may, optionally, also containone of the following members: --O--, --S--, --N═, --NH-- or --N(C₁ -C₆-alkyl)-; R²⁴ and R²⁵ independently of one another are each C₁ -C₆-alkyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₁ -C₆-alkoxy-C₁ -C₆ -alkyl or R²⁴ and R²⁵ together form a saturated orunsaturated 2- to 4-membered hydrocarbon chain which may carry an oxosubstituent, where one member of this chain may be replaced by a bridge--O--, --S--, --N═, --NH-- or --N(C₁ -C₆ -alkyl)- which is not adjacentto the variables Z¹ and Z², and where the hydrocarbon chain may carryone to three radicals, in each case selected from the group consistingof cyano, nitro, amino, halogen, C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl, C₁ -C₆-alkoxy, C₂ -C₆ -alkenyloxy, C₂ -C₆ -alkynyloxy, C₁ -C₆ -haloalkyl,cyano-C₁ -C₆ -alkyl, hydroxy-C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy-C₁ -C₆-alkyl, C₃ -C₆ -alkenyloxy-C₁ -C₆ -alkyl, C₃ -C₆ -alkynyloxy-C₁ -C₆-alkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -cycloalkoxy, carboxyl, (C₁ -C₆-alkoxy)carbonyl, (C₁ -C₆ -alkyl)carbonyloxy-C₁ -C₆ -alkyl and phenylwhich itself may be unsubstituted or may carry one to threesubstituents, in each case selected from the group consisting of cyano,nitro, amino, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxyand (C₁ -C₆ -alkoxy)carbonyl, and where the hydrocarbon chain may alsobe substituted by a fused-on or spiro-linked 3- to 7-membered ring whichmay contain as ring members one or two hetero atoms selected from thegroup consisting of oxygen, sulfur, nitrogen and C₁ -C₆-alkyl-substituted nitrogen, and which may, optionally, itself carry oneor two of the following substituents: cyano, C₁ -C₆ -alkyl, C₂ -C₆-alkenyl, C₁ -C₆ -alkoxy, cyano-C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl and (C₁-C₆ -alkoxy)carbonyl; R²⁶ is hydrogen, cyano, halogen, C₁ -C₆ -alkyl, C₁-C₆ -haloalkyl, C₁ -C₆ -alkoxy, (C₁ -C₆ -alkyl)carbonyl or (C₁ -C₆-alkoxy)carbonyl; R²⁷ is hydrogen, O--R³⁴, S--R³⁴, C₁ -C₆ -alkyl whichmay carry one or two C₁ -C₆ -alkoxy substituents, C₂ -C₆ -alkenyl, C₂-C₆ -alkynyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -cycloalkyl, C₁ -C₆-alkylthio-C₁ -C₆ -alkyl, C₁ -C₆ -alkyliminooxy, --N(R³²)R³³ or phenylwhich may be unsubstituted or may carry one to three substituents, ineach case selected from the group consisting of cyano, nitro, halogen,C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy and(C₁ -C₆ -alkoxy)carbonyl; R²⁸ is hydrogen, cyano, halogen, C₁ -C₆-alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl,(C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆ -alkoxy)carbonyl, --N(R³²)R³³, orphenyl which may itself carry one to three substituents, in each caseselected from the group consisting of cyano, nitro, halogen, C₁ -C₆-alkyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -alkenyl, C₁ -C₆ -alkoxy and (C₁ -C₆-alkoxy)carbonyl; R²⁹ is hydrogen, cyano, halogen, C₁ -C₆ -alkyl, C₁ -C₆-alkoxy, C₁ -C₆ -haloalkyl, (C₁ -C₆ -alkyl)carbonyl or (C₁ -C₆-alkoxy)carbonyl; R³⁰ is hydrogen, cyano, C₁ -C₆ -alkyl or (C₁ -C₆-alkoxy)carbonyl; R³¹ and R³⁴ independently of one another are eachhydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₂ -C₆ -alkenyl or C₂ -C₆-alkynyl, where the 4 last-mentioned groups may in each case carry oneor two of the following radicals: cyano, halogen, hydroxyl,hydroxycarbonyl, C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, (C₁ -C₆-alkyl)carbonyl, (C₁ -C₆ -alkoxy)carbonyl, (C₁ -C₆ -alkyl)carbonyloxy,(C₃ -C₆ -alkenyloxy)carbonyl or a 3- to 7-membered azaheterocycle whichis attached to the nitrogen atom via a carbonyl bridge and which may inaddition to carbon ring members also contain an oxygen or sulfur atom asring member; or (C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆ -haloalkyl)carbonyl,(C₁ -C₆ -alkoxy)carbonyl, C₁ -C₆ -alkylaminocarbonyl, di(C₁ -C₆-alkyl)aminocarbonyl, C₁ -C₆ -alkyloximino-C₁ -C₆ -alkyl, C₃ -C₆-cycloalkyl, phenyl or phenyl-C₁ -C₆ -alkyl, where the phenyl rings maybe unsubstituted or may themselves carry one to three substituents, ineach case selected from the group consisting of cyano, nitro, halogen,C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy and (C₁ -C₆-alkoxy)carbonyl; R³² and R³³ independently of one another are eachhydrogen, C₁ -C₆ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₃ -C₆-cycloalkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, (C₁ -C₆-alkyl)carbonyl, (C₁ -C₆ -alkoxy)carbonyl, (C₁ -C₆ -alkoxy)carbonyl-C₁-C₆ -alkyl, and the agriculturally useful salts and enol ethers of thecompounds I.
 2. A substituted 3-phenylisoxazoline of the formula I asclaimed in claim 1, where R⁸ is:1) hydrogen, hydroxyl, mercapto, cyano,halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -haloalkoxy, C₁ -C₆-haloalkylthio, C₁ -C₆ -alkylthio-(C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆-alkyl)iminooxycarbonyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, C₁ -C₆-alkoxyamino-C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkylamino-C₁ -C₆-alkyl, 2) C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, C₃ -C₆ -cycloalkoxy, C₃-C₆ -cycloalkylthio, C₂ -C₆ -alkenyloxy, C₂ -C₆ -alkenylthio, C₂ -C₆-alkynyloxy, C₂ -C₆ -alkynylthio, (C₁ -C₆ -alkyl)carbonyloxy, (C₁ -C₆-alkyl)carbonylthio, (C₁ -C₆ -alkoxy)carboxyloxy, (C₂ -C₆-alkenyl)carbonyloxy, (C₂ -C₆ -alkenyl)carbonylthio, (C₂ -C₆-alkynyl)carbonyloxy, (C₂ -C₆ -alkynyl)carbonylthio, C₁ -C₆-alkylsulfonyloxy or C₁ -C₆ -alkylsulfonyl, where each of the 17last-mentioned radicals may, optionally, carry one to threesubstituents, in each case selected from the group consisting ofhalogen,nitro, cyano, hydroxyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -alkoxy, C₃ -C₆-cycloalkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆ -alkynyloxy, C₁ -C₆ -alkoxy-C₁-C₆ -alkoxy, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylsulfinyl, C₁ -C₆-alkylsulfonyl, C₁ -C₆ -alkylideneaminooxy, oxo, ═N--OR¹⁸, the phenyl,phenoxy or phenylsulfonyl group, which may be unsubstituted or may carryone to three substituents, in each case selected from the groupconsisting of halogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl,C₁ -C₆ -alkoxy and (C₁ -C₆ -alkoxy)carbonyl, a group --CO--R¹⁹,--CO--OR¹⁹, --CO--SR¹⁹, --CO--N(R¹⁹)R²⁰, --OCO--R¹⁹, --OCO--OR¹⁹,--OCO--SR¹⁹, --OCO--N(R¹⁹)R²⁰ or --N(R¹⁹)--R²⁰, the group--C(R²¹)═N--OR¹⁸ ; 3) --CO--R²², --CS--R²², --C(NR²³)--R²², --C(R²²)(Z¹R²⁴)(Z² R²⁵), where Z¹ and Z² are each oxygen or sulfur,--C(R²²)═C(R²⁶)--CN, --C(R²²)═C(R²⁶)--CO--R²⁷,--CH(R²²)--CH(R²⁶)--CO--R²⁷, --C(R²²)═C(R²⁶)--CH₂ --CO--R²⁷,--C(R²²)═C(R²⁶)--C(R²⁸)═C(R²⁹)--CO--R²⁷, --C(R²²)═C(R²⁶)--CH₂--CH(R³⁰)--CO--R²⁷, --CO--OR³¹, --CO--SR³¹, --CO--N(R³¹)--OR¹⁸,--C.tbd.C--CO--NH--OR¹⁸, --C.tbd.C--CO--N(R³¹)--OR¹⁸,--C.tbd.C--CS--NH--OR¹⁸, --C.tbd.C--CS--N(R³¹)--OR¹⁸,--C(R²²)═C(R²⁶)--CO--NH--OR¹⁸, --C(R²²)═C(R²⁶)--CO--N(R³¹)--OR¹⁸,--C(R²²)═C(R²⁶)--CS--NH--OR¹⁸, --C(R²²)═C(R²⁶)--CS--N(R³¹)--OR¹⁸,--C(R²²)═C(R²⁶)--C(R²¹)═N--OR¹⁸, --C(R²¹)═N--OR¹⁸,--C.tbd.C--C(R²¹)═N--OR¹⁸, --C(Z¹ R²⁴)(Z² R²⁵)--OR³¹, --C(Z¹ R²⁴)(Z²R²⁵)--SR³¹, --C(Z¹ R²⁴)(Z² R²⁵)--N(R³²)R³³, --N(R³²)R³³ or --CON(R³²)R³³; R¹⁸ is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -cycloalkyl,C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, hydroxy-C₁ -C₆ -alkyl, C₁ -C₆-alkoxy-C₁ -C₆ -alkyl, C₁ -C₆ -alkylthio-C₁ -C₆ -alkyl, cyano-C₁ -C₆-alkyl, (C₁ -C₆ -alkyl)carbonyl-C₁ -C₆ -alkyl, (C₁ -C₆-alkoxy)carbonyl-C₁ -C₆ -alkyl, (C₁ -C₆ -alkoxy)carbonyl-C₂ -C₆-alkenyl, (C₁ -C₆ -alkyl)carbonyloxy-C₁ -C₆ -alkyl or phenyl-C₁ -C₆-alkyl, where the phenyl ring may, optionally, carry one to threesubstituents, in each case selected from the group consisting of cyano,nitro, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy and (C₁-C₆ -alkoxy)carbonyl; R¹⁹ is hydrogen, C₁ -C₆ -alkyl, C₃ -C₆-cycloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₁ -C₆ -alkoxy-C₁ -C₆-alkyl, (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkyl, (C₃ -C₆-alkenyloxy)carbonyl-C₁ -C₆ -alkyl, phenyl or phenyl-C₁ -C₆ -alkyl,where the phenyl group and the phenyl ring of the phenylalkyl group maybe unsubstituted or may carry one to three radicals, in each caseselected from the group consisting of halogen, nitro, cyano, C₁ -C₆-alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy and (C₁ -C₆ -alkyl)carbonyl;R²⁰ is hydrogen, hydroxyl, C₁ -C₆ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₆-alkoxy, (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkoxy, C₃ -C₆ -alkenyl or C₃-C₆ -alkenyloxy; R²¹ ishydrogen, halogen, C₁ -C₆ -alkyl, C₁ -C₆-haloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₃ -C₆ -alkenyloxy, C₁-C₆ -alkylthio, C₁ -C₆ -haloalkylthio, (C₁ -C₆ -alkyl)carbonyloxy, (C₁-C₆ -haloalkyl)carbonyloxy, C₁ -C₆ -alkylsulfonyloxy or C₁ -C₆-haloalkylsulfonyloxy, where the 11 last-mentioned radicals may carryone of the following substituents: hydroxyl, cyano, hydroxycarbonyl, C₁-C₆ -alkoxy, C₁ -C₆ -alkylthio, (C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆-alkoxy)carbonyl, (C₁ -C₆ -alkyl)aminocarbonyl, di(C₁ -C₆-alkyl)aminocarbonyl, (C₁ -C₆ -alkyl)carbonyloxy, C₁ -C₆ -alkoxy-(C₁ -C₆-alkyl)aminocarbonyl; a 3- to 7-membered azaheterocycle which isattached to the nitrogen atom via a carbonyl bridge and which may, inaddition to carbon ring members, also contain one oxygen or sulfur atomas ring member; (C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆ -haloalkyl)carbonyl,(C₁ -C₆ -alkoxy)carbonyl, (C₁ -C₆ -alkoxy)carbonyloxy, (C₁ -C₆-alkyl)carbonylthio, (C₁ -C₆ -haloalkyl)carbonylthio, (C₁ -C₆-alkoxy)carbonylthio, C₂ -C₆ -alkenyl, C₂ -C₆ -alkenylthio, C₃ -C₆-alkynyl, C₃ -C₆ -alkynyloxy, C₃ -C₆ -alkynylthio, (C₂ -C₆-alkynyl)carbonyloxy, C₃ -C₆ -alkynylsulfonyloxy, C₃ -C₆ -cycloalkyl, C₃-C₆ -cycloalkyloxy, C₃ -C₆ -cycloalkylthio, (C₃ -C₆-cycloalkyl)carbonyloxy, C₃ -C₆ -cycloalkylsulfonyloxy; phenyl, phenoxy,phenylthio, benzoyloxy, phenylsulfonyloxy, phenyl-C₁ -C₆ -alkyl,phenyl-C₁ -C₆ -alkoxy, phenyl-C₁ -C₆ -alkylthio, phenyl-(C₁ -C₆-alkyl)carbonyloxy or phenyl-(C₁ -C₆ -alkyl)sulfonyloxy, where thephenyl rings of the 10 last-mentioned radicals may be unsubstituted ormay themselves carry one to three substituents, in each case selectedfrom the group consisting of cyano, nitro, halogen, C₁ -C₆ -alkyl, C₁-C₆ -haloalkyl, C₁ -C₆ -alkoxy and (C₁ -C₆ -alkoxy)carbonyl; R²² ishydrogen, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₂ -C₆ -alkenyl, C₂-C₆ -alkynyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl or (C₁-C₆ -alkoxy)carbonyl; R²³ is hydrogen, hydroxyl, C₁ -C₆ -alkyl, C₃ -C₆-alkenyl, C₃ -C₆ -alkynyl, C₃ -C₇ -cycloalkyl, C₁ -C₆ -haloalkyl, C₁ -C₆-alkoxy-C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆-alkynyloxy, C₃ -C₆ -cycloalkoxy, C₅ -C₇ -cycloalkenyloxy, C₁ -C₆-haloalkoxy, C₃ -C₆ -haloalkenyloxy, hydroxy-C₁ -C₆ -alkoxy, cyano-C₁-C₆ -alkoxy, C₃ -C₆ -cycloalkyl-C₁ -C₆ -alkoxy, C₁ -C₆ -alkoxy-C₁ -C₆-alkoxy, C₁ -C₆ -alkoxy-C₃ -C₆ -alkenyloxy, (C₁ -C₆ -alkyl)carbonyloxy,(C₁ -C₆ -haloalkyl)carbonyloxy, (C₁ -C₆ -alkyl)carbamoyloxy, (C₁ -C₆-haloalkyl)carbamoyloxy, (C₁ -C₆ -alkyl)carbonyl-C₁ -C₆ -alkyl, (C₁ -C₆-alkyl)carbonyl-C₁ -C₆ -alkoxy, (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkyl,(C₁ -C₆ -alkoxy)carbonyl-C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio-C₁ -C₆-alkoxy, di(C₁ -C₆ -alkyl)amino-C₁ -C₆ -alkoxy, phenyl which may itselfcarry one to three substituents, in each case selected from the groupconsisting of cyano, nitro, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl,C₂ -C₆ -alkenyl, C₁ -C₆ -alkoxy and (C₁ -C₆ -alkoxy)carbonyl, phenyl-C₁-C₆ -alkoxy, phenyl-C₃ -C₆ -alkenyloxy or phenyl-C₃ -C₆ -alkynyloxy,where in each case one or two methylene groups of the hydrocarbon chainsmay be replaced by --O--, --S-- or --N(C₁ -C₆ -alkyl)-, and where eachphenyl ring may be unsubstituted or may itself carry one to threesubstituents, in each case selected from the group consisting of cyano,nitro, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₂ -C₆ -alkenyl, C₁-C₆ -alkoxy and (C₁ -C₆ -alkoxy)carbonyl, heterocyclyl, heterocyclyl-C₁-C₆ -alkoxy, heterocyclyl-C₃ -C₆ -alkenyloxy or heterocyclyl-C₃ -C₆-alkynyloxy, where in each case one or two methylene groups of thehydrocarbon chains may be replaced by --O--, --S-- or --N(C₁ -C₆-alkyl)-, and where each heterocycle may be 3- to 7-membered, saturated,unsaturated or aromatic and contains one to four hetero atoms selectedfrom the group consisting of two oxygen atoms, two sulfur atoms and 4nitrogen atoms, and is either unsubstituted or itself carries one tothree substituents, in each case selected from the group consisting ofcyano, nitro, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₂ -C₆-alkenyl, C₁ -C₆ -alkoxy and (C₁ -C₆ -alkoxy)carbonyl, or --N(R³⁵)R³⁶where R³⁵ and R³⁶ are each hydrogen, C₁ -C₆ -alkyl, C₃ -C₆ -alkenyl, C₃-C₆ -alkynyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy-C₁-C₆ -alkyl, (C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆ -alkoxy)carbonyl, (C₁ -C₆-alkoxy)carbonyl-C₁ -C₆ -alkyl, (C₁ -C₆ -alkoxy)carbonyl-C₂ -C₆ -alkenylwhere the alkenyl chain may additionally carry one to three halogenand/or cyano radicals, or are phenyl which may be unsubstituted or mayitself carry one to three substituents, in each case selected from thegroup consisting of cyano, nitro, halogen, C₁ -C₆ -alkyl, C₁ -C₆-haloalkyl, C₃ -C₆ -alkenyl, C₁ -C₆ -alkoxy and (C₁ -C₆-alkoxy)carbonyl, or where R³⁵ and R³⁶ together with the linkingnitrogen atom form a saturated or unsaturated 4- to 7-memberedazaheterocycle which, in addition to carbon ring members, may,optionally, also contain one of the following members: --O--, --S--,--N═, --NH-- or --N(C₁ -C₆ -alkyl)-; R²⁴ and R²⁵ independently of oneanother are each C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -alkenyl, C₃-C₆ -alkynyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl or together are a saturatedor unsaturated 2- to 4-membered hydrocarbon chain which may carry an oxosubstituent, where one member of this chain may be replaced by a bridge--O--, --S--, --N═, --NH-- or --N(C₁ -C₆ -alkyl)- which is not adjacentto the variables Z¹ and Z², and where the hydrocarbon chain may carryone to three radicals, in each case selected from the group consistingof cyano, nitro, amino, halogen, C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl, C₁ -C₆-alkoxy, C₂ -C₆ -alkenyloxy, C₂ -C₆ -alkynyloxy, C₁ -C₆ -haloalkyl,cyano-C₁ -C₆ -alkyl, hydroxy-C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy-C₁ -C₆-alkyl, C₃ -C₆ -alkenyloxy-C₁ -C₆ -alkyl, C₃ -C₆ -alkynyloxy-C₁ -C₆-alkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -cycloalkoxy, carboxyl, (C₁ -C₆-alkoxy)carbonyl, (C₁ -C₆ -alkyl)carbonyloxy-C₁ -C₆ -alkyl and phenylwhich may itself be unsubstituted or may carry one to threesubstituents, in each case selected from the group consisting of cyano,nitro, amino, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxyand (C₁ -C₆ -alkoxy)carbonyl, and where the hydrocarbon chain may alsobe substituted by a fused-on or spiro-linked 3- to 7-membered ring whichmay contain as ring members one or two hetero atoms selected from thegroup consisting of oxygen, sulfur, nitrogen and C₁ -C₆-alkyl-substituted nitrogen, and which may, optionally, itself carry oneor two of the following substituents: cyano, C₁ -C₆ -alkyl, C₂ -C₆-alkenyl, C₁ -C₆ -alkoxy, cyano-C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl and (C₁-C₆ -alkoxy)carbonyl; R²⁶ is hydrogen, cyano, halogen, C₁ -C₆ -alkyl, C₁-C₆ -haloalkyl, C₁ -C₆ -alkoxy, (C₁ -C₆ -alkyl)carbonyl or (C₁ -C₆-alkoxy)carbonyl; R²⁷ is hydrogen, O--R³⁴, S--R³⁴, C₁ -C₆ -alkyl whichmay carry one or two C₁ -C₆ -alkoxy substituents, C₂ -C₆ -alkenyl, C₂-C₆ -alkynyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -cycloalkyl, C₁ -C₆-alkylthio-C₁ -C₆ -alkyl, C₁ -C₆ -alkyliminooxy, --N(R³²)R³³ or phenylwhich may be unsubstituted or may carry one to three substituents, ineach case selected from the group consisting of cyano, nitro, halogen,C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy and(C₁ -C₆ -alkoxy)carbonyl; R²⁸ is hydrogen, cyano, halogen, C₁ -C₆-alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl,(C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆ -alkoxy)carbonyl, --N(R³²)R³³ or phenylwhich may itself carry one to three substituents, in each case selectedfrom the group consisting of cyano, nitro, halogen, C₁ -C₆ -alkyl, C₁-C₆ -haloalkyl, C₃ -C₆ -alkenyl, C₁ -C₆ -alkoxy and (C₁ -C₆-alkoxy)carbonyl; R²⁹ is hydrogen, cyano, halogen, C₁ -C₆ -alkyl, C₁ -C₆-alkoxy, C₁ -C₆ -haloalkyl, (C₁ -C₆ -alkyl)carbonyl or (C₁ -C₆-alkoxy)carbonyl; R³⁰ is hydrogen, cyano, C₁ -C₆ -alkyl or (C₁ -C₆-alkoxy)carbonyl; R³¹ and R³⁴ independently of one another are eachhydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₂ -C₆ -alkenyl or C₂ -C₆-alkynyl, where the 4 last-mentioned groups may in each case carry oneor two of the following radicals: cyano, halogen, hydroxyl,hydroxycarbonyl, C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, (C₁ -C₆-alkyl)carbonyl, (C₁ -C₆ -alkoxy)carbonyl, (C₁ -C₆ -alkyl)carbonyloxy,(C₃ -C₆ -alkenyloxy)carbonyl or a 3- to 7-membered azaheterocycle whichis attached to the nitrogen atom via a carbonyl bridge and which may, inaddition to carbon ring members, also contain one oxygen or sulfur atomas ring member; or are (C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆-haloalkyl)carbonyl, (C₁ -C₆ -alkoxy)carbonyl, C₁ -C₆-alkylaminocarbonyl, di(C₁ -C₆ -alkyl)aminocarbonyl, C₁ -C₆-alkyloximino-C₁ -C₆ -alkyl, C₃ -C₆ -cycloalkyl, phenyl or phenyl-C₁ -C₆-alkyl, where the phenyl rings may be unsubstituted or may themselvescarry one to three substituents, in each case selected from the groupconsisting of cyano, nitro, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl,C₁ -C₆ -alkoxy and (C₁ -C₆ -alkoxy)carbonyl; R³² and R³³ independentlyof one another are each hydrogen, C₁ -C₆ -alkyl, C₃ -C₆ -alkenyl, C₂ -C₆-alkynyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy-C₁ -C₆-alkyl, (C₁ -C₆ -alkyl)carbonyl, (C₁ -C₆ -alkoxy)carbonyl, (C₁ -C₆-alkoxy)carbonyl-C₁ -C₆ -alkyl, (C₁ -C₆ -alkoxy)carbonyl-C₂ -C₆-alkenyl, where the alkenyl chain may additionally carry one to threehalogen and/or cyano radicals, or are C₁ -C₆ -alkylsulfonyl, (C₁ -C₆-alkoxy)carbonyl-C₁ -C₆ -alkylsulfonyl, phenyl or phenylsulfonyl, wherethe two phenyl rings may be unsubstituted or may themselves carry one tothree substituents, in each case selected from the group consisting ofcyano, nitro, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₆-alkenyl, C₁ -C₆ -alkoxy and (C₁ -C₆ -alkoxy)carbonyl, or R³² and R³³together with the linking nitrogen atom are a saturated or unsaturated4- to 7-membered azaheterocycle which, in addition to carbon ringmembers, may, optionally, contain one of the following members: --O--,--S--, --N═, --NH-- or --N(C₁ -C₆ -alkyl)-.
 3. A herbicidal composition,comprising a herbicidally effective amount of at least one substituted3-phenylisoxazoline of the formula I or an agriculturally useful salt orenol ether of I, as claimed in claim 1, and at least one inert liquidand/or solid carrier and, optionally, at least one surfactant.
 4. Aprocess for the preparation of herbicidally active compositions, whichcomprises mixing a herbicidally effective amount of at least onesubstituted 3-phenylisoxazoline of the formula I or an agriculturallyuseful salt or enol ether of I, as claimed in claim 1, and at least oneinert liquid and/or solid carrier and, optionally, at least onesurfactant.
 5. A method for controlling unwanted vegetation, whichcomprises allowing a herbicidally effective amount of at least onesubstituted 3-phenylisoxazoline of the formula I or an agriculturallyuseful salt or enol ether of I, as claimed in claim 1, to act on plants,their habitat or on seeds.